


Share Alike

by BlueNeutrino



Series: Isosceles Triangles [5]
Category: Supernatural
Genre: Aftercare, Anal Beads, Anal Plug, BDSM, Begging, Biting, Blindfolds, Bondage, Bondage and Discipline, Catheters, Chains, Cock & Ball Torture, Cock Cages, Collars, Creampie, Crossdressing Kink, Dildos, Dirty Talk, Dom Castiel, Dom Sam, Dom/sub, Double Anal Penetration, Double Penetration, Enemas, Erotic Electrostimulation, Facials, Feathers & Featherplay, Feeding Kink, Felching, Fluff On Occasion, Food Sex, Grossly Inaccurate and Erotic Medical Procedures, Heartbeat Kink, Humiliation, Inventive Enemas, Kink Negotiation, Leashes, M/M, Medical Kink, Nipple Clamps, Nipple Play, Nude Photos, Object Insertion, Oral Sex, Orgasm Denial, Other, Painplay, Plot What Plot/Porn Without Plot, Praise Kink, Prostate Massage, Punishment, Rimming, Roleplay, Rope Bondage, Sensation Play, Shower Sex, Sibling Incest, Spanking, Speculums, Sub Dean, Threesome - M/M/M, Urethral Play, Watersports, Whipping, Wincestiel - Freeform
Language: English
Status: Completed
Published: 2014-03-27
Updated: 2015-08-20
Packaged: 2018-01-17 05:04:00
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 25
Words: 56,691
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1374808
Author URL: https://archiveofourown.org/users/BlueNeutrino/pseuds/BlueNeutrino
Summary: <blockquote class="userstuff">
              <p>Dean is a sub. That part, at least, is simple. The problem is that Sam and Cas are both Doms, and they don’t always like to share. For Dean’s sake, they try to come to an arrangement.</p><p>(Currently at over 50,000 words of pure porn as I work my way through various kinks. No plot to be found here, just glorious three-way smut.)</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Multi-chapter Wincestiel PWP, because I'm trying something new.
> 
> For the purposes of this fic, they're on hiatus from hunting. Not necessarily a long one, but it's going to become obvious very quickly they don't have much time or interest in that when there's other fun stuff to do. I never said this was going to be realistic! But hopefully it's enjoyably kinky.

**Summary for the Chapter:**

> Kinks: kink negotiation, cock cages, butt plugs.

“We’ve reached an agreement," Sam announced as both he and Cas surveyed Dean from across the table, who looked back at them in curiosity. He wasn't entirely sure why they'd called him in here to talk to him, but he hoped this meant they’d somehow worked out their recurring arguments over who got to Dom him and how. While he loved them both deeply, and he knew they loved him as well as each other, he found it frustrating how in the bedroom they struggled to get along. While things seemed fine between them when they were dealing with everyday life or hunting and keeping things strictly business, when it came to sex - specifically, sex with Dean - fights frequently seemed to break out. In trying to convince each other of what Dean would enjoy most, they invariably only ended up making things less enjoyable for him, and he was growing tired of it. He hated seeing them fight. If this meant a resolution to that, then as far as he was concerned, it was the best news he’d had in ages.

“Great,” Dean prompted him further. “In what way?”

“There’s a few rules we’ve decided to lay down for you and for each other, so that we share you fairly,” Sam elaborated. “Would you like to hear them?”

Dean nodded. “Go on.”

“Firstly, while in the bunker you’re to be naked at all times. That way, neither of us can ask you to undress without the other agreeing, and you’re on display for both of us whenever we want. Do you consent to that?”

The frankness of the suggestion was unexpected, but it sent a sudden rush of blood to Dean’s groin. Displaying himself for them was always fun, and he felt very dirty and very turned on at the idea of doing it nearly all the time. He licked his lips and nodded. “Yes.”

“Secondly,” Cas picked up where Sam left off, “We want you to wear this on a near-permanent basis.” From below the table he produced an object, and then placed it in front of Dean for him to see. It was a chastity cage, consisting of leather straps attached to metal rings designed to fit snuggly over his penis and balls. Near the strap that would go round his ball sac were two tiny padlocks, ensuring that once locked, only the person with the key could take it off. “We’ve added an additional lock to it,” Castiel explained. “I will have one key, Sam will have the other. That way, if either of us wants to get you hard or play with you, we both have to agree. Do you consent to that as well?”

Dean swallowed. He’d worn a cock cage for them on occasion before, but the idea of keeping one on 24/7 was thrilling. “Yes.”

“Okay, our next term is butt plugs,” Sam continued. “You’ll wear one each day, alternating between one that Cas will insert, and one that I will insert. Whosever day it is is the one that you must go to if you want it adjusted or removed. Agreed?”

Dean nodded enthusiastically.

“We’ve also reached an agreement on who will shower you,” Cas then resumed. “We’ve worked out a schedule of days when you’ll shower with either one of us, and the days you’ll shower with us both. Any changes to that schedule have to be agreed by both of us. Yes?”

Dean again nodded his consent.

Sam took over his turn to explain. “Right, and then that brings us on to penetration and blowjobs. Whoever gets to fuck you in one session does not get to suck you, and vice versa. Turns will alternate between fucking sessions, not between days. How does that sound?”

“Good. Yes, please”

“Finally,” Cas completed, “Any punishments or rewards we deliver to you will be negotiated by us on a case by case basis. Your safeword still applies in all events and to all conditions we've just outlined. All these terms will become active as of now, if you agree to them?”

Eagerly, Dean croaked his enthusiastic confirmation. “Yes, I agree.”

“Good,” Sam said, leaning back in his chair. “Clothes off, then. We want to see you.”

Both Cas and Sam stared at him expectantly, and obediently, Dean stood to walk round to the other side of the table and began stripping down in front of them. He could feel their eyes on him, roaming appreciatively over his bare skin, and he loved how dirty it made him feel. Once he’d finished, he stood naked and on display before them, as they both surveyed him with appraising looks.

“Very nice,” Sam commented, glancing at Dean’s semi-hard dick. “But don’t you dare get a full erection before we put the cage on you. We’d hate to have to punish you so soon.”

The dirty talk didn’t really help discourage Dean’s cock, which gave another twitch. Dean blushed and tried not to imagine what delicious punishment he might receive.

“I shall put on the chastity cage, Sam will insert the butt plug,” Cas announced commandingly, picking up the device. “Now come here and show me your cock.”

Dean did as he was told, presenting his dick to Cas and trying not to get any harder in order for it to be put on.

Cas frowned at it and tutted. "You're a filthy slut, aren't you? Already getting hard? Well, we'll have to put a stop to that before it goes any further." He started to slide the rings of the cage over Dean's partially stiff dick, pausing as the glans came to nestle up against the bar across the end. He had to lift Dean's balls in order into insert them into the ring meant for them, and he then hitched up the cage further so that Dean's balls were cradled tightly by a steel ring and a leather strap. Cas pushed Dean's dick down between his legs as he pulled the leather strap tight around his scrotum and snapped the dual lock into place. Dean felt the extra weight pulling his cock down and confining him nicely.

Cas leaned back to admire the view and then grinned up at Dean, reaching out to the table to retrieve the keys Sam had just put down. "This one's for me," he said as he picked one up and held it out for Dean to see, and then slipped it into the inside pocket of his coat. "And that one's for Sam." Sam picked up the other key and placed it into his jeans pocket.

Dean felt a slight anxiety that they were both putting the keys in places where it seemed possible they could get lost, but he supposed they were doing it to tease him on purpose.

"Right," Sam said, taking over from Cas. He was holding up an object he'd just produced from under the table, and had been absently preparing with lube to aid insertion while he watched Cas work. The butt plug was blue silicone and shaped somewhat like a tapered lightbulb with a flanged end, so that once inserted, only the narrowest part was accessible from Dean's entrance while the rest plugged him up snuggly.

"Bend over the table and spread your ass cheeks for me, Dean," Sam ordered, and Dean went to stand by the table and then reached behind him to pry apart his cheeks. He leaned forward, allowing Sam better access to his hole. They'd done this once or twice before, but never with the intention of leaving the toy in semi-permanently, and Dean delighted in the kinkiness.

He felt Sam press a moistened finger into his entrance, causing a slight sting as he stretched Dean enough to begin pressing in the plug. Dean's cock twitched from the sensations, but as he felt blood rush to his dick as it tried to harden, a tight, uncomfortable pressure began to squeeze his balls. He bit down on his lip in discomfort as the cage prevented him from hardening fully, but felt happy that he was pleasing both Cas and Sam by doing this.

Sam's fingers pulled at his ring as he pushed the plug in further, stretching him out as the widest part of the plug breached his entrance. As it passed through the hole, Dean's body readily sucked the rest of the toy into him. Dean gasped, feeling the plug stuffing him up as the flare rested just outside his rim.

Sam gave his ass a slap as he pulled back to watch Dean's cheeks close up. "All done," he said, indicating Dean could turn round again. "But if we think we need extra security, we will add a belt to keep that in." He and Cas then exchanged a smirk.

"Okay, Dean, carry on," Cas said, "You can go about your day as normal, but if you're in the same room as me or Sam, we expect a nice display from you. Shyness or attempts to cover up will not be tolerated.

Dean nodded, wondering how he was meant to go back to a normal day when all he wanted was more attention from both of them on his skin and in his ass and around his cock, but delayed gratification didn't work like that.

Both of them had begun to leave the room, each still smirking, and Dean tried to go back to doing something normal even if his brain was whirling so much he couldn't remember what he'd been doing before this conversation. But even so, nothing was quite as much a turn on as seeing them both agree on sexual practices involving him, and even if he had to wait now, Dean knew the sweet payoff would be well and truly worth it later on.


	2. Chapter 2

**Summary for the Chapter:**

> Kinks: collars and leashes, punishment, spanking

It was a perfectly mundane task. For all the advanced fifties era mod-cons the bunker was equipped with, a dishwasher wasn’t one of them, and doing the dishes manually was one of the best attempts at continuing as normal Dean could make. He was working through them steadily, alone in the kitchen, and it took him completely by surprise when he felt a sudden presence behind him. His fingers faltered in their scrubbing as a warm hand came to rest on the bare skin of his hip.

“Why are you stopping?” he heard Cas’ low voice growl in his ear. The sneaking up out of nowhere must be an angel thing. “Don’t you dare stop on my account.”

Dean quickly resumed his work, although he was finding it very hard to concentrate as he felt Cas’ hands exploring more of his skin. A hot mouth pressed to the juncture of Dean’s neck and shoulder in order to nip and suck at him, before biting down harder against the edge of his collarbone. Dean drew in a sharp breath of pleasure from the pain.

As Cas continued kissing and licking at him he realised he’d been scrubbing the same completely clean plate for the past minute or so, completely lost in the sensations Cas was inflicting.

The angel’s lips pulled away for a moment as he raised his fingers to Dean’s neck, gently caressing down the line of Dean’s throat, and then Dean felt a larger movement from the angel behind him as he lifted something up towards Dean’s head. The scent of leather filled his nose, and then he felt something stiff being fitted around his neck. Again his hands faltered, and he gasped in excitement as the collar was secured into place.

This time Cas didn’t seem to mind him stopping as Dean heard the sound of a leash being clipped onto the collar, and Cas tugged on it slightly so that Dean felt a firm pressure against his throat. “Much better,” Cas growled, the side of his head pressed against Dean’s so that Dean felt his breath on his ear. “Now you’re mine.”

A hand then moved to the back of his thigh, sliding upwards and dipping between his legs to drag fingers into the crack of Dean’s ass. Dean felt his cock throb, the restriction from the chastity cage tight and painful as he was unable to get hard.

Cas began to spread his cheeks, a finger nudging at the anal plug that was just slightly protruding from his hole. He rubbed a slow, teasing circle around it. “Do you want me to take it out, Dean?” he whispered huskily in his ear, “Would you like me to remove it so I can have a play around inside you instead?”

Dean’s head was spinning and his breathing was coming fast and shallow, aching to feel Cas’ fingers moving and rubbing inside his channel. He knew he wasn’t supposed to, since Sam had been the one to put the plug in, but he was just so desperate to feel stimulation on his prostate if he couldn’t on his dick that he found himself agreeing. “Yes,” he whimpered needily. “Please, Cas.”

The angel tutted at him, putting on a tone of shock. “But it’s Sam’s plug. He’d be so upset if he found out we’d taken it out with asking.”

“He doesn’t have to know…” Dean breathed desperately.

“You’d do that to your own brother?” Cas growled in disapproval, fingers moving down from the plug to slide further forward and poke at Dean’s balls through the gaps in the cage. “How terrible of you, Dean. I think that deserves punishment. We should tell Sam.”

He then pulled his hand out from between Dean’s legs and gave a tug on the leash, forcing Dean to follow him out of the room. Dean felt a sudden thrill as he realised this whole thing must have been a conspiracy between the pair of them, and he eagerly anticipated his punishment.

They found Sam sat at the table back in the main room, reading something, and Cas cleared his throat as they approached. Sam looked up, frowning at the sight of Dean being dragged on his leash towards him. “Dean has something to tell you, Sam,” Cas said, pulling Dean forward to present to him.

Dean blushed and looked at the floor, feeling helplessly turned on.

Sam’s frown deepened, and he stood up to take a few paces towards his brother and study him in more detail. “What do you have to tell me, Dean?”

Dean’s voice was quiet when he answered. “I tried to get Cas to take out your butt plug, Sammy.”

A look of hurt crossed Sam’s face. “But that plug is _mine,_ Dean,” he said, his exaggerated anger immediately sending blood to futilely try and fill Dean’s cock. “I put it in for you. I gave you pleasure with it, and this is how you repay me?”

“I’m sorry, Sammy,” Dean pleaded.

“After everything Cas and I have done to please you, you try to turn us against each other.” He gave a disappointed shake of his head. “I think that deserves punishment. Don’t you agree, Cas?”

“I do,” Dean heard Cas growl out as he stepped forward to hand over the leash to Sam.

Sam took hold of it and then gave it a tug to pull Dean over towards the table. “Very well, then,” he said as he fastened the end of the leash to one of the table legs, and then went over to one of the nearby cabinets to retrieve something from the drawers. Dean didn’t know what he was doing, but as he saw him pull out a leather spanking paddle that he’d concealed in one of the lesser-used compartments, Dean felt a rush of excitement.

Sam gave a disapproving click of his tongue, beating the end of the paddle into his own palm a few times as he strode purposefully back towards Dean. “Turn around and bend over,” he instructed, and Dean repositioned himself to bend over the table and offer his ass up for punishment, barely able to contain himself.

Across the table he saw Cas walk round to stand opposite him, smirking as he undid his fly and then pulled out his cock. He began to stroke himself as he enjoyed the view, and Dean felt his face flush as he found the sight so incredibly hot.

The paddle gently caressed the backs of Dean’s thighs and buttocks once or twice as Sam continued to berate him. “I’m disappointed in you, Dean,” he said, dragging the leather over Dean’s skin and causing him to tremble in anticipation. “Do you know how much you hurt me trying to go behind my back?”

The sensation of the firm material against his skin suddenly became absent, and then there was the sound of something being dragged quickly through air with a _whoosh_ before it slapped hard against his skin. Dean yelped, savoring the sting of it.

“That’s how much you hurt me, Dean,” Sam said, pulling back the paddle and then bringing it down again in another hard slap. Again Dean cried out in joy, ass smarting as he watched Cas furiously pump himself across the table. His eyes watered from the pain, but he was loving every second of it.

Sam looked down at the redness beginning to spread over Dean’s cheeks and smiled in satisfaction. “I think you need to understand that,” he said, hitting once more even harder. “That kind of behavior will not be tolerated.” One final smack, the hardest of all, and as Dean screamed unashamedly Cas grunted and came.

The sight of Cas spilling all over himself sent another hot surge of blood to Dean’s cock, hurting almost as much as his ass as the cage forced it to stay down. He gave a whimper as he heard Sam move in closer behind him, setting down the paddle.

Warm hands gently caressed his buttocks, tender and soothing after the pain as they checked that not too much damage had been done. Dean felt a warm body pressing into his back, and hot breath ghosted over Dean’s cheek as Sam drew his face in close to his. “Have you learned your lesson, Dean?” he purred softly.

“Yes, Sammy,” Dean whimpered back, “I’m sorry for hurting you, Sammy.”

“Good boy,” Sam said, lovingly pressing a kiss to Dean’s temple. “Now Cas, does he get to taste your come?”

“I think so,” Cas replied in a husky voice, tucking his soft cock back into his pants as he walked round the table towards Dean. Dean’s eyes flickered hungrily up at him as Cas raised a come-coated hand to Dean’s mouth. Sticky fingers pressed against his lips, parting them and pressing inwards. “Suck,” Cas ordered, and Dean obediently drew the digits further into his mouth and lapped them clean with his tongue. Cas’ taste was both sweet and salty, distinctly different from both Sam’s and his own, and Dean savored every drop.

“Well done,” Cas said once clean, pulling his fingers from Dean’s mouth with a slick pop. His thumb grazed over Dean’s cheek affectionately before he pinched Dean’s chin and tilted it upwards to look at him, his expression becoming much more stern. “Now if you want that cock cage to come off at any point in the next few days, you’d better be on your best behavior.”

“That means doing as you’re told,” Sam reiterated as he checked the fastenings securing the leash to the table legs. “Now stay.”

They both then turned to exit the room, satisfied grins on their faces as they left Dean tied to the table, who was almost unable to process how unbelievably hot they were when they worked together and felt his restrained dick aching for more.


	3. Chapter 3

**Summary for the Chapter:**

> Kinks: face-fucking, threesomes

It was four deliciously agonizing days before Dean got so much as a hint that the chastity cage might soon be allowed to come off. They were having dinner, Dean sat naked between Cas and Sam with only a napkin spread over his lap and the collar still around his neck. He felt incredibly horny from the days he’d spent without release, but despite his frustration he’d been on his best behavior, hoping that would soon earn him a reward. He wasn’t allowed to feed himself so his hands were tied behind his back, and Sam and Cas were taking it in turns to feed him pasta from their own forks. As they finished, plates almost empty, Sam and Castiel exchanged a conspiratorial look.

“You know, Cas,” Sam said loudly, ensuring Dean was paying close attention. “I think Dean has been very good these past few days. Should we reward him?”

Dean’s dick suddenly twitched at the suggestion, holding his breath as he thought that tonight it might finally get freed.

Cas smirked back, casting a wicked glance over Dean as he licked his lips. “I don’t know,” he said teasingly, “I think maybe he needs to do something more for us before we let him come. Perhaps he should suck us both off?”

Dean squirmed silently in his seat, not wanting to speak without permission in case it ruined his chances of going through with what seemed like a very enticing proposal.

Sam grinned. “I think that sounds good. What do you think, Dean?”

“Yes,” Dean gasped enthusiastically, his cock aching for them to lavish it in attention if he got to blow them both first. “Yes, please. I can do that.”

“Very eager, aren’t you, you little whore?” Cas teased, and then he picked up the end of Dean’s leash again and tugged on it. “Alright then, let’s get you to the bedroom.”

They left the dishes on the table, deciding they had better things to do tonight, and Cas and Sam led Dean through the bunker to their room. “Kneel,” Sam ordered him once inside, so that Dean knelt at the foot of the bed, and they both took out their keys to his cock cage and set them down just beside him. Cas then tied Dean’s leash to the bedpost before he and Sam stripped off in front of him. Dean watched them, jealous of their erect cocks that were revealed as pants fell away, while at the same time thinking they were both so gorgeous and so hot.

Having finished undressing, Sam and Cas came to stand in front of Dean, staring down at him on the floor with his hands still bound. He looked so pretty in his restraints, his naked body beautifully on display for them to please and enjoy however they wished.

“You can go first, Cas,” Sam said to the angel, and then took a step back as Cas approached Dean and positioned his cock in front of Dean’s mouth.

“Open wide, Dean,” Cas ordered, and Dean stretched his lips as far apart as he could so that Cas could insert his cock into him. The angel’s dick was thick and hot, sliding quickly to the back of his mouth, and Dean fought to overcome his gag reflex as the tip grazed the back of his throat. “That’s it,” Cas muttered encouragingly, his hands moving to Dean’s head to hold him in place as he gently began to thrust. He took it steadily, ensuring he pulled back enough each time to allow Dean to breathe, and they soon reached a rhythm of Dean sucking in breaths through his nose in between repeatedly swallowing Cas. Dean was bobbing his head in opposition to the motion of Cas’ hips, ensuring each movement was as deep as possible, and he was eagerly licking over Cas’ length for more of the delicious taste. They managed to draw it out for several minutes before Dean finally felt Cas’ cock jerk and spill come into his mouth, and he swallowed down as much of it as possible.

Cas then slowly pulled back, a smile on his face, and he leaned down to kiss Dean’s forehead. “Good boy,” he said, “Now if you want your reward, you have to suck off Sam too. Can you do that, Dean?”

Dean nodded, licking what remained of Cas’ come from his lips. “Yes, I can do that.”

“Alright,” Cas said, stepping aside to let Sam take his place. The younger Winchester was far less gentle, wasting no time in grabbing hold of Dean’s hair to pull his head back as he started to thrust roughly into Dean’s mouth. His balls smacked against Dean’s chin and his cock repeatedly slammed down Dean’s throat as he fucked his face. Dean thought he might start to choke, but Sam finished much more quickly and aggressively than Cas, spurting his come into Dean after just a couple of minutes. As he pulled back, Dean gasped for breath, and a small amount of come and saliva dribbled from his mouth and clung to his chin in a string of mucus. Sam gave him a pleased look. “Don’t want me to start going soft on you now, do you?” he said as he bent down to remove Dean’s collar. “Getting this off should be kindness enough, but because Cas thinks you deserve a reward for being so good, we’re going to be even nicer.”

He then went to untie Dean’s hands, and Dean felt a flutter of excitement and relief as he was freed from the restraints. His cock was painfully throbbing for attention that he hoped it would soon get.

Sam lifted him up forcefully by the shoulders to sit him on the end of the bed, and then spread his knees apart. He gazed appreciatively down at the sight of Dean’s member struggling to swell in its cage, before looking up at his face. “You did well, Dean,” he said as he reached up to wipe the last of his come from the corners of Dean’s mouth. “Now let’s take a look at your cock.” He picked up his key and settled himself down between Dean’s legs to free his aching member, unfastening one of the locks. He then held out his hand for Cas’ key, who gave it to him so that he could finish unlocking the cage. The second lock opened with a faint click, and Dean drew in a breath of anticipation at the thought he was finally about to get what he’d been craving for days. Sam steadily slipped the rings off of Dean’s dick, which immediately began to harden as it was freed from his restraints. “There you are. How does that feel?” Sam said as he smiled down at it, dipping his head to press a kiss to the tip.

“ _Oh god_ …suck me Sammy, _please_ …” Dean moaned needily, and Sam tutted.

“I can’t, Dean,” he apologised, “It’s Cas’ turn. But today I own your ass.”

He shifted himself to sit down beside Dean’s spot on the end of the bed, simultaneously manoeuvring Dean to get up and stand in front of him. He positioned Dean’s ass before him so that he had access to his hole, spreading Dean’s legs either side of his knees. Cas, meanwhile, had worked himself to hardness again and moved to kneel between Dean’s legs, grinning at the hunter’s cock. “And this is all mine,” he teased, extending his tongue to lick at it and lap the drops of pre-come from the tip. Dean whimpered.

Cas had picked up a bottle of lube from the nightstand which he now handed to Sam, who began to smear it over his fingers and his own cock as he rubbed himself back to hardness. Once fully slicked, he moved his hands to spread Dean’s ass cheeks and feel for the end of the plug poking out of his hole. There were grooves on the end to improve his grip for easier removal, and he worked his fingers in around the plug to pinch it and slowly pull it out. Dean moaned as the thick plug stretched him out, feeling incredibly empty as his hole was evacuated, but Sam’s slick fingers quickly pushed into him to replace it. The younger Winchester slotted two digits into Dean, which he scissored a couple of times to check Dean was still properly stretched, and proceeded to smear more lubricant inside him. Once he had decided Dean was properly prepared, he then pulled out his fingers and gripped onto Dean’s hips to guide him into position. Dean slowly lowered himself into Sam’s lap, feeling his brother’s thick cock poking against his entrance. There was a slight burn as the head breached his rim, slowly easing an inch or so inside, and then Dean sank all the way back onto Sam with a gasp. Sam’s length slid all the way up into him in one go, and Dean cried out from the delicious sensation of being stuffed full of dick.

Cas had been watching Dean’s face as Sam penetrated him, thinking how beautiful he looked as long eyelashes fluttered against his cheeks and his pink lips parted in moans of ecstasy. Cas licked his own lips as he bent closer to Dean’s cock, hungry for the taste of it, and then wrapped his mouth around the head. The action took Dean by surprise, who had been so lost in the feeling of Sam’s cock that he gasped in shock at the sudden wet heat that had enveloped his own dick. Cas slid his mouth all the way down Dean’s length, drawing him into the back of his throat, and Dean trembled in joy.

He began to rock his hips, thrusting down onto Sam’s cock and up into Cas’ mouth, and the three of them quickly fell into a steady rhythm as Cas and Sam worked together to pleasure Dean. Dean felt utterly euphoric, his cock and his asshole rejoicing from the careful attention they were now being given after the days they’d spent caged and plugged. He felt completely filled by Sam, the hardness of him delightfully stretching his walls and banging against his prostate, while Cas was warm around him and his throat tight against the head of Dean’s cock.

Dean quickened their pace, Sam and Cas adjusting to the speed he set as he squirmed desperately between them. Sam felt Dean’s walls clamping down around him, making him see stars, and he moved his hands to flick and play with Dean’s nipples while he clamped his mouth down on Dean’s shoulder and sucked. Cas tugged furiously on his own cock as he enjoyed the taste of Dean in his mouth, the hunter’s dick delicious on his tongue. Both of them concentrated on bringing Dean to climax first, and after a minute or so of vigorous dual stimulation, Dean came with a cry into Cas’ mouth. His hips jerked roughly upwards and Sam followed him, the feel of Dean’s body convulsing and clamping down even tighter on his cock enough to send him over the edge. Dean trembled once more as he felt himself filled with Sam’s seed, and as Cas felt Dean’s hot, salty come slide down his throat, he finished himself with a couple of rough strokes.

Filled with come on the inside, as well as coated in it as Cas’ splashed all over his thighs and hips, Dean gave a sated sigh. Spent, he collapsed back down against Sam’s chest, the both of them breathing heavily. His cock plopped from Cas’ mouth, who straightened up and leaned in to kiss the bridge of Dean’s nose as the brothers sank back down onto the bed. Castiel clambered up to kneel on top of them, easing his head down to press his mouth against Dean’s, allowing him to taste his own come. He wanted Dean to know just how delicious he was, and he was pleased to find the hunter licked hungrily at the pearly liquid on his lips. Cas then went to retrieve the cock cage, and his hand nudged Dean’s soft dick as he prepared to confine him again.

“I’m going to put this back on now,” he said softly to Dean, easing the rings back over Dean’s cock and balls. Dean didn’t protest, thinking that what he had just experienced made the cage all the more worth it. “But you’ve been very good,” Cas assured him, “If you keep this up, we might even let you come twice next time.” With Dean’s dick snuggly nestled in his restraints, Cas snapped the lock closed again and then lay himself down against the two brothers. His hand draped over both Sam’s and Dean’s waists, and his head came to rest against Dean’s chest.

Dean could feel Sam’s heart beating against his back, as quickly as his own, which he was sure Cas could feel through his ribs. The sensation was comforting, creating an almost tangible connection between the three of them as their heart rates slowed and synchronised. As Dean lay warm and safe between Sam and Castiel, sated and beginning to drift off to sleep, he contemplated that while there had been many unfortunate things in his life, he was lucky to have two people who loved him this much.


	4. Chapter 4

**Summary for the Chapter:**

> Kinks: shower sex, food sex, feeding kink (but not fat kink)

“Good morning, Dean.”

Dean felt himself being gently awakened by the sound of a soft voice in his ear. He was enveloped in warmth, and he could feel the smooth skin of two firm, hot bodies pressed against his back and chest. Light breath tickled his cheek as he sleepily eased his eyes open to see Sam smiling down affectionately at him. His brother pressed a kiss to his brow. “Did you sleep well?”

“Like a baby,” Dean replied groggily, turning his head a little as he felt Cas moving beside him. The angel’s hand shifted over his waist and then Cas pressed his face against Dean’s neck to nuzzle at his jaw, nipping his skin slightly as Dean could feel him smiling against him.

“How are you feeling, Dean?”

“Great,” Dean sighed contentedly. “You know I love having you two get along like this.”

Sam smiled, pressing a kiss to his lips. “I’m glad our arrangement makes you happy.”

Dean felt a hand creeping between his thighs, and it took him a moment to figure out if it was Sam or Cas. Turned out it was Cas. His hand nudged Dean’s confined cock, lifting it slightly and feeling its weight inside the cage. “How’s things doing in there?”

Dean thought about the answer for a moment. “Tight.”

“Does your cock like it?”

“Very much.”

“Good.” He felt Cas growl against his throat as the angel’s soft cock rubbed against his thigh. Sam had moved a hand to his ass and was gently stroking it.

“Would you like us to take a shower with you, Dean?” he asked.

“Isn’t it Cas’ turn?” Dean replied uncertainly, unsure if he was going to get in trouble for the wrong answer, but Cas smiled.

“Sam is welcome to join us.”

“Then yes please.”

Cas grinned, pulling his lips away from Dean and propping himself up on his elbow. “Okay, but just one thing first.” He reached over to the nightstand to pick something up, and then held it in front of Dean for him to see. “Turn over. I need to put this in.” He was holding his butt plug, which was black and slightly longer and narrower than Sam’s.

Dean shuffled to roll over onto his front, delighting in the feel of Cas’ hands on his ass cheeks, stroking them tenderly before spreading them apart. Some of Sam’s come from last night leaked out of him, still wet from the heat inside Dean’s body, and Sam watched it with a grin. He liked the thought that his seed was about to be plugged up inside his brother, as well as keeping Dean’s channel nice and slick. Cas was very careful with Dean’s hole as he put the plug in, almost managing it painlessly, and Dean let out a contented sigh as his entrance was blocked up. Cas let his cheeks close again and then cupped them, gently rubbing as he leaned down and kissed the dip at the base of Dean’s spine. “There we are,” he murmured softly, sitting up again. “Now shall we go get you washed?”

Still all naked, the three of them clambered out of bed and headed to the bathroom. Cas started up the shower, testing the water temperature while Sam turned to Dean. “Do you need to use the bathroom?”

Dean nodded, feeling that his bladder was somewhat full. “Yes.”

“Okay. Let me help you,” Sam offered as they walked over to the toilet. Sam stood behind Dean and then reached round to grab his cock through the cage and aimed it into the bowl. Dean pissed, the holes in the cage meaning he could do so in a sanitary fashion, and then Sam shook the final drops off the end and flushed once he’d finished. “Do you feel dirty?” Sam muttered in his ear.

Dean nodded, thinking that having someone else help him piss made him feel wonderfully filthy.

“That’s because you _are_ dirty, Dean. You’re a dirty little cockwhore who’s still covered in last night’s dried come. Why don’t we go get you cleaned up?” Sam replied as he pulled Dean towards the shower, the three of them moving to stand beneath the stream of steaming water.

Dean was never permitted to wash himself, and Cas or Sam always had to make sure they got him cleaned in all the right places. Now, Sam had begun to work some soap into a lather between his fingers and was scrubbing it over Dean’s back, the pressure delightfully firm and slippery. He scraped his fingernails over Dean’s skin, and Dean sighed in pleasure.

Cas, meanwhile, had knelt down to rub shower gel over Dean’s legs, making sure to cover as much of his skin as possible as he scraped away his come from yesterday. His hands ran up the insides of Dean’s thighs, and Dean squeezed his legs together in joy at the feeling of Cas’ fingers there. Cas began to straighten up again, pressing his mouth against Dean’s stomach and then licking a stripe along his wet abdomen as he stood. Once he’d reached Dean’s chest, he moved his mouth over Dean’s right nipple, sucking at it firmly before giving it a bite. It hurt, and Dean gasped in pain, but then Cas immediately eased up the pressure of his teeth and pressed a kiss against the nub to soothe it. He started rubbing soapy suds over Dean’s stomach and sides while Sam began to work on his shoulders and arms.

After they scrubbed him down a little more and cleaned themselves, Sam picked up a bottle of shampoo and dispensed some onto his hands, before starting to work it through Dean’s hair. Dean closed his eyes as he lost himself in the pleasure of Sam’s strong fingers massaging his scalp, while hot water washed over his skin and he felt the solid mass of Sam’s body against his back. Sam’s dick was partially hardened and was poking into the back of his thigh, while in front of him he could feel Cas standing in close with his almost-soft member squashed against Dean’s leg. Cas had snaked a hand round his hip to his back and then down to cup one of his ass cheeks, firmly kneading it while Sam rubbed at his head.

“God, that feels so good,” Dean murmured, eyes fluttering open to see Cas smiling and looking pleased.

“We aren’t quite done cleaning you up yet,” he said, moving his hand to scoop some of the bubbles from Dean’s hair, and then moving to deposit it just above his cock. He started to shampoo Dean’s pubic hair, and Dean felt his cock swell by the small amount that it was able within its cage.

He heard Sam chuckle in his ear. “Do you like that, Dean?”

“Yes,” Dean breathed, and Sam bit down on his earlobe and gave it a tug.

“Well, you be a good boy a bit longer and let us finish cleaning you, and there might be a reward.”

They stood beneath the streaming shower head for a little while longer, enjoying the heat of the water and the presence of each other. Once they were all three clean and devoid of soap suds, Sam shut the water off and they stepped out of the shower. Sam and Cas dried themselves off first, leaving Dean standing naked and dripping as he wasn’t allowed to do it himself. They both loved the way he looked when soaking wet; droplets of water clinging to his smooth skin and running over the toned lines of his body, pooling in the dips and curves that they both loved to touch. He began to shiver slightly from the moisture evaporating heat away from his skin, but it was good discipline for him to suffer the discomfort for a short while.

Once Sam and Cas were mostly dry, they pulled on bathrobes and began to towel Dean down. He wasn’t permitted to put clothes back on, so they both rubbed talc on his skin to help him dry out, showering him in kisses all over his body as they did so.

“Alright, breakfast,” Sam said once they’d finished, leading the way out of the room to the kitchen. Dean obediently followed, and Cas kept an arm around his waist as a milder measure of control since they’d decided to leave the collar off.

As they reached the kitchen they sat him down at the table, while Cas started to make the coffee and Sam began to prepare breakfast. “How do pancakes sound?” he asked, and Dean licked his lips.

“Yes please,” he answered.

Sam looked over to Cas. “Does he get pancakes, Cas?”

“That depends,” Cas said, “Will he have room for it if he wants some cock first?”

Sam’s eyes flashed deviously as he looked back at Dean, liking the sound of that suggestion. “Would you like to taste some cock first, Dean?”

Dean swallowed, eyes widening. “Yes _please_.” He sounded even more enthusiastic about that suggestion than the former.

“Alright,” Sam said while Cas continued preparing the coffee, as he went to stand beside Dean. He parted his bathrobe to pull out his cock, giving it a couple of rubs to make it fully hard. Dean eyed it eagerly. “Kneel down,” Sam instructed, so that Dean slipped off his chair to kneel on the floor. “Here,” he said, offering his cock out to Dean, who obediently took it in his mouth. Sam moved a hand to his head and began to stroke his damp hair. “Just a few mouthfuls, we don’t want you getting full up.” Dean continued to suck at him eagerly, and Sam had to get him to ease up. “Don’t worry about making me come, Dean. There’ll be time for that later. For now, you just have a quick taste.”

Dean pulled his head away, looking quite ready to keep going. “Don’t worry, you can have a taste of Cas too,” Sam reassured him as Cas set three mugs of coffee down on the table. Sam returned to the stove to start making the pancakes as Cas went over to Dean and began to rub himself hard, ready to give Dean his second helping.

“Are we having syrup with breakfast?” Sam said with a devilish grin, picking up a bottle of the stuff.

Cas looked over to him, about to say that syrup with pancakes was usually a good idea, but then took his double meaning and grinned as he accepted the bottle that Sam was offering. “Of course,” he said, turning to look again at Dean, who seemed very excited at this development. Cas popped the top off the bottle and then drizzled a small amount on the end of his cock. Dean licked his lips as he watched the golden fluid run sticky and viscous over Cas’ shaft, looking positively delicious. “Here you are, Dean,” Cas offered, as Dean closed his mouth around his cock and began to lick at it. The syrup was sweet on his tongue, but not half as sweet as he thought Cas tasted. “You just get me clean for now, and there’ll be plenty of come for you to swallow later on,” Cas said as Dean’s tongue finally finished lapping away the last of the stickiness, and Cas gently pushed his head away from his dick. “Okay, you can sit back down at the table now.” Dean did so, still hungry to taste more cock in his mouth, but he was getting used to being told to wait. He found that the process was usually very rewarding in the end.

As Cas tucked himself away again inside his bathrobe, Sam placed down a fresh stack of pancakes in front of Dean, and then proceeded to drizzle it with syrup. The smell was sweet and delicious in Dean’s nose, and his stomach growled. Sam heard it and chuckled. “Hungry, aren’t you? Now, can you be trusted not to feed yourself? Or do I need to tie your hands again?”

Dean shook his head. “No, I promise I’ll be good.”

“Okay,” Sam said as he and Cas took a seat either side of Dean. “See to it you are.”

They each had their own set of cutlery and began to cut pieces of pancake that they fed to Dean, occasionally taking mouthfuls for themselves. Dean was thoroughly enjoying it, thinking that this was a perfect morning after a perfect night before. Although his cock occasionally still ached as it itched to be hard and free, Dean couldn’t deny that having the cage on had made things even more enjoyable when it finally came off. He was learning the value of patience very quickly.

“Would you like more syrup?” Cas offered, and Dean nodded. Cas drizzled a little more on the forkful of pancake his was wielding, before pushing it into Dean’s mouth. Dean gratefully chewed on the spongy sweetness, but Cas still had hold of the bottle and he allowed a little more syrup to drip out onto Dean’s shoulder.

Dean moaned around the fork in his mouth in delight as Cas pressed his mouth to his skin to lick it away. “Delicious,” Cas murmured. “Would you like to try, Sam?”

“I think I will,” Sam replied as he took the bottle from Cas, and proceeded to allow more syrup to drizzle down over Dean’s chest. Dean squirmed from pleasure as Sam’s teeth grazed at his collarbone and began to lick it off, chasing runaway droplets down his chest and sucking them away. His mouth closed over Dean’s left nipple, gently pinching the nub between his teeth and giving it a tug. The sensation gave Dean a buzz. “Well, Dean, you’re the best thing I’ve tasted for breakfast in a while,” Sam said, giving Dean’s nipple one final lick as he pulled back and took a sip of his coffee.

Cas fed Dean another mouthful of pancake. “Thirsty?” he asked.

Dean nodded again.

“Okay, here you are,” Cas said as he picked up Dean’s coffee mug before raising it to Dean’s lips and tilting it, who tried his best to swallow down the hot liquid without spilling. Some still dribbled out onto his chin and he wondered if he was going to get in trouble, but Cas just licked it away with a kiss. They were both being very kind to him this morning.

Breakfast took them considerably longer than it might have done as they gradually worked through the stack of pancakes between them, Cas and Sam often more interested in tasting Dean than they were the food. Eventually, the plate was empty, and Cas picked it up to take it to the sink.

“You’ve been very good, Dean,” Sam said to him with a smile, looking very pleased with the whole situation. Dean thought he felt the same. Sam and Cas pleasuring him together without arguing was the best arrangement he could have hoped for, and he was more than willing to be obedient for anything if it meant they were getting along.

“You were a very good boy last night,” Sam continued, “But how long do you think you can make this behavior last for? Will you still be good for us in more… _testing_ situations?”

A strange look had entered his eyes and Dean wasn’t too sure what he was talking about, but it vaguely registered with him that although he’d seen Cas pick up the plates, he still couldn’t see him at the sink despite it being in his line of sight. His tongue didn’t move quickly enough to reply to Sam before a blindfold descended on his eyes, and with a thrill he felt his hands being roughly pulled and tied behind his back.

**Notes for the Chapter:**

> I just want to say thanks so, so much to everyone who's been reading this or has left kudos! I'm having a lot of fun writing it and it's nice to see people are enjoying it even though I didn't expect it to get much attention. Wincestiel is kind of a new thing for me because it's taken me a while to get over my incest squick, but I do love the thought of Cas and Sam domming the hell out of Dean and I suspect things are going to get much rougher and kinkier in the next chapter.


	5. Chapter 5

**Summary for the Chapter:**

> Kinks: bondage, suspension, blindfolds, cock cages, CBT

He was lying in the dark. Or at least he thought it was dark, difficult as it was to tell through the blindfold. One thing he was sure of was that he was in the bunker’s dungeon; he could tell the route Cas and Sam had taken on the way down despite his disorientation, and it wasn’t as if they could have put him anywhere else. They’d at least laid out a mattress on the floor for him, but he knew the feel of the metal cuffs round his wrists and ankles, stretching his limbs out tautly, if not painfully, so that the chains rattled as he tried to move. The cool air caressed his bare skin with a chill, and he knew they’d left him in the deepest, most underground part of the bunker.

He also suspected he was alone. After they done tying him up, Sam had left him with a warning that the more noise he made, the longer he’d have to wait, and then Dean had heard the sound of footsteps receding and the entrance sliding shut behind them. So now he’d been lying cold in the dark for an hour or more, the sense of excitement at what they were going to do to him next mixed with more than a little nervousness and trepidation. He didn’t mind a bit of bondage or pain for pleasure, but the not knowing was nerve wracking. It was starting to get to him, the longer he was left down here on his own, feeling tense and isolated. He suspected they’d left some kind of listening device down here with him, if they were paying attention to how much noise he made, but so far all they would have heard was his heavy, slightly quickened breathing. He was trying to be good. He liked being good for them, especially when they were getting along so well for him, and after this testing scenario he desperately wanted a reward.

The listening device meant he could use his safeword if things ever became too much, but despite the thought having crossed his mind a couple of times when he’d given over to fleeting fits of panic, he’d refrained. If he bailed out now, he wasn’t ever going to get the sweet, sweet pleasure he was sure would follow. So he lay quietly, trying to keep his breathing under control and staying as calm as possible.

His efforts were rewarded, at length, by the sound of the doorway sliding open again and two pairs of footsteps approaching. It had been about two hours, by Dean’s estimate.

“Hello Dean,” he heard Cas’ voice say nearby, and then the mattress below him shifted as someone knelt down upon it. “How have things been for you down here?”

He didn’t know if there was a wrong answer to that. If he let them know he hadn’t enjoyed it, they might leave him here longer. “Quiet,” he answered carefully.

Cas chuckled. “Yes, things were. You did very well to make so little noise. I do hope you’ll make a little more when we’re having our way with you.”

That sentence was enough to send a thrilled rush of blood to his cock. He felt fingers on his lips, and then Sam’s voice growled. “Open up, Dean.”

He did so, wondering what was going on since the blindfold meant he still couldn’t see, although there was apparently enough light for the others. He felt a small pellet being placed down on his tongue, and then a glass of water was being lifted to his lips. “Swallow,” Sam ordered, and although Dean was a little nervous and confused as to why they were making him swallow a pill, he did as he was told.

Sam chuckled slightly as he watched Dean gulp it down, enjoying the sight of his throat muscles contracting and thinking about the delights those same muscles worked on his cock. “Now Dean, you’re going to have to be very brave, and very good for us,” Sam said, pressing a kiss down over Dean’s clavicle and then kneeling back to look at him.

Dean didn’t know what he was talking about at first, but soon he began to feel a tightness in his groin, blood rushing to his cock as it tried to get hard despite the lack of stimulation. He felt a flutter of trepidation ripple through his gut as he realised the pill was Viagra.

Pain started to squeeze at his balls as his cock elongated and filled, held back by the tight metal bars of the cage. Dean grunted and gasped. It fucking _hurt._ Granted, it had hurt a little before every time he’d gotten aroused only to find his cock trapped and held down, but the discomfort had usually been enough to make him soften again. With the Viagra in his system, he didn’t think that was going to be possible.

His cock was trying to swell, way too large for the cage that held it, and he felt the leather straps cutting across his balls as his entire dick throbbed and twitched. “ _Fuck_ Sam, take it off…” he murmured through clenched teeth, his cock fighting hard against its restraints as it tried to rise. “It _hurts…_ take it off…”

He sounded distressed, but with a hint of excitement seeping through in his tone. Sam turned to Cas. “Should we take the cage off him, Cas? It hasn’t been very long since we let him out.”

Cas addressed Dean in his reply. “You know the word, Dean. If you want to, just say it and the cage comes off. But if you don’t want, be brave for us a little longer, okay?”

Dean hissed in pain. He was tempted. Tempted to just snap his safeword at them and then they’d take the restraints away, but then he knew he’d just be left with his dick hard and throbbing, and they wouldn’t give it their usual careful attention if he cut things short now. If he absolutely _had_ to get off, they'd let him, but he didn’t want to spoil what they had going on by quitting when things got a little tough. “No, I’ll be brave,” he said through gritted teeth, trying to stop himself writhing on the mattress as he futilely thrust his hips upwards as if he could shake the cage off.

“Don’t worry, Dean, we won’t leave you like this forever,” Sam reassured him, after watching him squirm for a short while longer. “But you have to learn good behavior. Now, who owns your cock?”

Dean knew what the expected answer was. “You do,” he grunted, words distorted from pain and hoping that they’d take pity on him.

“What was that, Dean?”

“You do! You own my dick. It’s all yours.”

Sam seemed satisfied. “That’s right, so we get to decide what happens to it,” he said, leaning in close to Dean to nip at his earlobe before turning to address Cas. “Cas, I think he’s learned. What shall we do with him now?”

Cas looked down at Dean’s beautifully writhing body below him, deciding that there was no need for his torment to last much longer. “Would you like me to make you go down now, Dean?” he offered. “I’m an angel. I have the power to do that.”

Dean didn’t want Cas to fucking make it go down. He wanted the cage off and their hands and mouths all over his rock solid dick, working him until he came. He almost yelled for them to just take it off and suck him, but a good submissive didn’t make demands. “Yes,” he gasped, thinking he’d take a fucking antidote over this.

"Yes what?"

”Yes, _please_.”

“You just hang on a minute longer, Dean, then I will,” Cas said.

The next minute was agonizing, Dean’s cock feeling like it was being squeezed by a razor-toothed vice, but then he felt fingers pressing against his lips again. They were pulled tight as his teeth were clenched, but he opened up readily as Cas inserted his index and middle fingers into his mouth. “Suck me like another pill,” he instructed, “And I’ll make the pain go away.” Dean’s lips tightened around Cas as he licked desperately at his fingers, the angel’s skin salty on Dean’s tongue.

It took a few seconds to work, which Dean was sure Cas was doing deliberately, but after about half a minute he felt the tightness around his dick easing as it slowly went limp again. “There you are,” Cas muttered as he retracted himself from Dean’s mouth, gently stroking the side of Dean’s face as he did so. “All better.”

“Well done, Dean,” he heard Sam say as he pressed a kiss to his stomach. “You did well to last that long. Now we’re just going to check that everything’s okay.”

Sam’s hands moved to Dean’s crotch, and Dean felt the movement of the cage as Sam now – and of course it would be _now_ rather than earlier – inserted his key into the lock and opened it. Dean’s cock was far too limp and aching for Dean to get excited about the cage now coming off.

“Cas, shall I unlock him so we can make sure his dick’s alright?” Dean heard Sam ask.

“Of course,” Cas replied as he gave Sam his key, “Don’t want any damage done to that pretty little cock.”

The second lock opened, and then Sam slid the cage away so that Dean’s cock flopped down between his legs. Sam’s hand immediately went to fondle it, giving it a couple of strokes, but Cas’ ‘medicine’ had rendered it limp and unresponsive. “Look at how soft it is,” Sam remarked, continuing to play with it and delighting in its pliant sponginess. “Cas, do you want to have a feel?”

Dean then felt another hand move to cup his cock. “Oh Dean, you’re so _squashy_ ,” Castiel commented in amusement, managing to almost bend Dean’s dick in half. Dean whimpered slightly, thinking that the sensations did indeed feel good even if his body couldn’t properly respond to them.

A fingertip moved under his dick to nudge his balls, which were somewhat tender and swollen from denied release. “How does that feel, Dean?” Sam asked.

“Sore,” Dean replied honestly, and was relieved as he felt Sam’s mouth descend to lick at his balls, the wetness and warmth of his tongue soothing them.

“There, there,” Sam muttered into the crease between Dean's cock and ball sack, the hum of his voice causing a slight tickle on the sensitive skin. “Let us take good care of you.” He ran his tongue over Dean’s cock, still hanging limply between his legs as Cas played with the head. Dean felt Cas roll back his foreskin, and then fingertips pressed teasingly into his slit. The sensations made Dean tremble. Having his dick fondled and sucked while completely soft was an unusual but not at all unwelcome feeling.

“It doesn’t look like there’s any harm done,” Cas delivered his assessment, letting Dean's member fall from his grip with a final swipe of his thumb over the tip. “Your cock’s in excellent shape, Dean. Tough and strong, just like you. That kind of resilience is going to be useful later.”

Those teasing words were enough to stir a swirl of excitement in Dean’s stomach, despite his present discomfort.

“Yes, it will,” Sam agreed, pulling his mouth away from Dean’s genitals, much to Dean's disappointment. “I think we should give him a rest for now. Maybe leave the cage off for a bit. It seems a shame to hide something so pretty away.” He admired the sight of Dean's flaccid cock for a moment longer as he cupped it in his palm, feeling the heaviness it retained despite being soft and limp. He then placed it down against Dean's stomach, and both he and Cas enjoyed the sight of how it rolled into a more natural position, curling slightly from a small bend near the tip. Dean felt the weight of it resting on his abdomen, and he wished he could get hard again so he could give Sam and Cas something nice to watch.

A moment later he felt weight shift off the mattress again as Sam and Cas got up. “Now Dean,” he heard Cas say from higher up above him. “You be good for us and don’t make any noise. You’ll want to keep all those lovely moans of yours saved up for tonight.”

Then Dean heard the sound of their footsteps leaving him again, the door opening and closing with a creak, and he wondered just what they had in store for him that he was expected to be so loud. Whatever it was, it was sure to be delicious and dirty and exciting. Despite everything, the thought made his cock give a twitch.


	6. Chapter 6

**Summary for the Chapter:**

> Kinks: e-stim, vibrators, orgasm denial, punishment, strapping

When they finally came back for him, several hours later, neither of them spoke. Instead they set to work on him immediately, warm hands grasping onto his body to manoeuvre and position him without a word. The first thing Dean was aware of was his head being lifted and a ball gag forced into his mouth, which was strapped in tightly before one of them then put a hand around his waist to lift him to his feet while the other adjusted the chains. It seemed he was being shifted from a horizontal position to a standing one, and he heard the chains rattle as they were detached from their moorings on the floor and instead were hoisted over the hooks Dean knew were embedded in the ceiling. There was a pulley system he'd seen in the dungeon on his less fun trips down here, and now he felt his arms being pulled upwards over his head as the cuffs were winched higher - presumably by Cas, if he judged correctly that the muscle tone pressed against his chest belonged to Sam.

It was impressive how in tandem they were, moving Dean where they wanted him without saying a word to each other. This had clearly been carefully planned out. With his arms stretched out above his head to an extent that was slightly strained but not uncomfortable, Dean suddenly felt the mattress being kicked out from under him. The support around his waist was eased away, leaving the chains holding him up as his feet struggled for purchase on the ground. A grunt slipped past his ball gag as he realised he was pulled too high and his legs spread too far apart to place his feet comfortably on the floor, but he could stand on tiptoe without the pressure being too great anywhere on his body to hurt. As he regained his balance, he felt a fingertip drag its way down his cock - Cas', judging from the thickness and the sharpness of the nail that scraped lightly over his skin - which was at last starting to harden again. Dean let out a muffled moan, buzzing with excitement.

After a moment or two longer he felt the heat radiating from a warm body stood just in front of him, and then hands reached behind the back of his head to pull off the blindfold. The fabric fell away from Dean’s eyes to reveal Sam standing in front of him, completely naked and with an approving look on his face as he cast his eyes up and down Dean’s body. Cas was standing a few feet behind him, and Dean looked up to see the angel run his tongue over his lips hungrily at the sight of him.

“Very nice, Dean,” Sam said, enjoying the display of Dean’s cock working its way back to hardness. He reached out a finger to touch the tip, and Dean thrust his hips forward as an invitation for Sam to close his entire fist around him. Sam pulled his hand back abruptly, giving a chuckle. “Now then, let’s not rush.” Once satisfied Dean would keep still, he returned his finger to stroke over Dean’s slit, teasing out a couple of drops of pre-come. Dean breathed out a heavy moan around the plastic ball stuffed in his mouth. “You’ve been waiting for that, haven’t you?” Sam teased as he withdrew his finger again. “Well, we’ve got an even bigger treat lined up.” He then turned to Cas, who had picked something up from the floor and now brought it forward. It was a small box with various dials on the face and several leads protruding from it, most with small pads attached to the end and one with two connected rubber rings. Dean felt his cock twitch in anticipation as he realized what it was.

Grinning, Sam and Cas began to attach the leads to him, placing electrodes on the underside of his balls and the insides of his thighs, as well as one further back on his perineum. Sam then slipped the conductive rings over his cock, keeping one close to the base and the other just under the head. While Sam fitted those in place, Cas raised himself to the level of Dean’s chest, producing two clover clamps for him to see. He reached out a hand to Dean’s left nipple, doing each one in turn as he rubbed his thumb over the nub to tease it into a peak, before securing the clamp into place. They pinched Dean’s nipples tightly, and already he’d begun to love the feeling before Cas began to attach a chain across them and gave it a tug to pull them down. “That’s right,” Cas murmured playfully in his ear. “Sam gets everything between your legs. I get your nipples and your ass.” He then proceeded to move himself to stand behind Dean, a hand creeping between Dean’s ass cheeks to nudge at the end of the butt plug. “Shall I replace this with something a little more fun?”

Dean nodded vigorously, and Cas chuckled slightly as he started to pry out the plug. Dean couldn’t see what he did with it once it was removed, but the strangely empty feeling in his hole was quickly replaced as something cool, hard and slick was inserted into him. “Just wait until we turn that on,” Cas growled, and a moan of anticipation shook through Dean’s chest.

“Now then, Dean,” Sam said from between his legs. “Are you ready?”

Dean couldn’t nod enthusiastically enough, impatient for the feel of the electric current running through him. Sam grinned wickedly, switching on the box and turning a dial so that Dean felt a soft buzz surge through him, concentrated intensely between his legs. He let out a moan through the gag.

“Louder, Dean,” Cas ordered, and Dean obeyed.

As a reward, Cas slid his hand over Dean’s ass cheeks to grasp the end of the vibrator and turn it on. The rush of sensations below his waist made Dean jerk his hips violently.

“More?” Sam offered, taking Dean’s delighted moans as an indication to turn up the current.

The volume of the sounds coming from Dean increased even further as the tingling through his thighs and genitals intensified, and his cock jerked violently against his stomach. “Now Dean, don’t you dare come yet,” Sam growled. “We’re going to make this last.”

They did, teasing him for several minutes with variation on the current and speed of the stimulation being applied, making his body squirm beautifully for them to watch. Dean's thighs clenched together and his hips bucked, eyes wide from pure euphoria. After a while, Cas stepped up closer behind Dean to nibble at the spot just under his ear and whispered softly to him, “Now Dean, I’m going to take the vibrator out. Then I’m going to _fuck you._ And I want you to be very, very loud for me, okay?” His hands moved to unfasten the ball gag, pulling it out of Dean’s mouth as a train of saliva followed. He discarded it somewhere behind him, keeping his face pressed close to Dean’s. “Do you think you can do that?”

Dean nodded, stretching his jaw a little to get used to working it again, and then murmured, “ _Yes._ ” His voice was low and breathy with lust.

“Good boy,” Cas said, nipping at his earlobe, and then began to ease the vibrator out. He didn’t turn it off, and Dean squirmed and yelped as the vibrating length exited him. “Not yet,” Cas reprimanded. “Save all those moans for me.”

Almost as soon as the dildo had been removed and switched off, Dean felt the warm head of Cas’ cock pressing against his entrance, already slicked up with lube and ready to sink into Dean’s stretched out hole. Cas moved his hands to grasp Dean’s hips, holding him still as he made the first thrust into him. Dean didn’t hold back on the cry of pleasure that escaped him.

Cas gave a tug on the chain across Dean’s nipples, biting into his neck as he repeatedly rocked his hips forwards into Dean’s ass. Sam was sat on the floor, watching them with a grin, and he turned up the current even higher to prompt more yells from Dean. The sight was delicious, but Sam took care not to overdo it. Cas quickened his pace, delight etched onto his face as he felt Dean clamping down around him with a force prompted by the jolts of electricity rushing through his cock and between his legs. The angel was thrusting roughly, his breathing quick and heavy while Dean’s eyes had fluttered shut and he looked to be on the brink of ecstasy.

“Don’t you dare come yet, Dean. Not without my permission,” Sam reminded him harshly.

Dean was trying. He really was, but all the sensations were just becoming too much. As much as he tried to hold it back, and tell his cock to be good because Cas and Sam were being _so so_ good to him, the moment he felt Cas spurting inside him was enough to finish him. He gave a final cry, as loud as he could make it, and came all over his chest.

Cas let out a sated sigh, pulling away so that his soft cock fell from Dean’s hole followed by a trickle of come. Dean was still breathing heavily, and although his cock had softened post-ejaculation, the pulses of current still running through it were causing it to convulse and twitch, preventing it from falling limply between his legs. When the power was switched off a moment later, Dean let out a disappointed whimper.

Sam stood up, crossing over to Dean with a stern look on his face, and Dean knew that his disobedience was now going to mean trouble.

Sam reached out to pinch his chin and tilted Dean’s face up to look at him. “I thought I told you not to come?”

Dean’s eyes fluttered to the ground apologetically. “I’m sorry, Sam. I couldn’t help it.”

Sam tutted at him. “We won’t keep giving you nice things if you can’t show us you’re grateful, Dean. Now we’re going to have to punish you.”

Bending down, he started to remove the come-coated rings from Dean’s cock and peeled away the electrodes from his skin, setting them to one side as he studied Dean’s limp member hanging down between his legs. Once finished, he straightened up again. “Cas?”

The final word was directed at the angel, who was still stood behind Dean and now held something out for Sam to take. “Here.”

Sam collected it from him and held it up for Dean to see: a wide leather belt, that he was now going to use for spanking. Dean licked his lips.

“Do you consent to your punishment, Dean?”

Dean nodded. “Yes, Sammy. I’ve been bad. Punish me.”

Sam grinned wickedly before walking around to stand behind Dean. Dean could see neither of them as he waited for the first blow to land, making the anticipation even more delicious.

“This is what happens,” Sam said, and then the air was suddenly wrenched apart with a _whoosh_ culminating in a harsh smack as the belt slammed against Dean’s skin. He yelled out in joy from the pain, his ass stinging like hell.

“When you don’t,” Sam continued, another blow landing hard across his cheeks, and Dean tried to make his cries as loud as possible to make up for his disobedience.

“Do as you’re told.” A final blow landed, hard enough that Dean thought he felt the edge of the strap draw blood, as something wet began to trickle down towards his thighs. He let out a whimper, loving how much it hurt.

“There,” Sam said, satisfied, before walking round to stand in front of Dean again. “Now to make up for what you’ve just done, we’re going to start all over again, and you’re going to let me suck you.”

Dean’s cock had only had a few minutes to recover from his last orgasm, but already he could feel it getting hard again as Sam knelt down between his legs and flicked his tongue across the head. “Hurry up, Dean,” Sam said impatiently, waiting for him to fully harden while he palmed himself absently. “You had no problem coming quickly.”

Within the next few seconds Dean’s dick had filled again, and Sam immediately wrapped his lips around it. Cas had moved to stand behind Dean, firmly placing his hands on his hips to hold him still for Sam. As Sam’s tongue pressed into his slit and his warm mouth slid up and down Dean’s length, Dean let out a whimper. He wanted more, his hole feeling aching and empty while everything else was so intense. “Oh god, Cas, finger me, please…” he pleaded, but Cas gave a disapproving tut at him.

Considering his ass checks were bleeding, opening Dean up right now probably wasn’t a good idea, but Sam wouldn’t have allowed it anyway. “No, Dean,” Cas declined, sensibly and reprovingly. “You disobeyed Sam, so now you’re going to come from the feel of his mouth on your cock, and that alone.”

Dean grunted and gasped, trying to thrust his hips forwards to heighten the sensations on his dick, but Cas held him still. Sam really was quite an expert with his tongue, running it over Dean’s shaft and licking at the sensitive spot just below the head while his mouth sucked all around Dean's member, before pulling it in further in order to deepthroat him. Sam took his time, not wanting Dean to finish early again, and it was several minutes before Cas took the signal to whisper permission in Dean’s ear. “Okay, now you can come.”

Dean did, spilling his seed all the way down Sam’s throat with a gasp. Sam lapped it up eagerly, not wasting a drop as he finally pulled his mouth away from Dean’s cock, being sure to catch the final pearly beads clinging to the tip. He then straightened up, and finished himself with a few rough tugs to splash his come over Dean's chest, mixing with what was left from earlier.

“Much better,” Sam said with a smile, licking his lips and giving Dean a pleased look. “Now let’s go get you cleaned up.”

With the session ended, they both started to take him down and uncuff him, helping him stand and providing affectionate strokes across his skin. They removed the nipple clamps and didn’t replace the butt plug or the cock cage, deciding that this had been intense enough for one day. Dean was still covered in come, and they wiped him down with a clean towel before helping him out of the dungeon.

A short while later they’d brought him back to the bedroom, Cas easing him down on his front onto the bed in order to see to the cuts on his ass. Sam pulled on some pajamas and then went to bring them a damp cloth and a first aid kit in order for Cas to take care of Dean. After giving them to Cas, he then gently stroked Dean’s hair as he checked that he was okay. “Are you alright, Dean?”

Dean nodded. “I’m fine.”

“Did you have fun?”

“Yeah, it was great.”

Sam smiled. “Good,” he said, bending down to kiss Dean’s temple. “Can I leave you with Cas? He’ll take care of you and I’ll go make us all hot chocolate, then we can put a movie on. How does that sound?”

Dean couldn’t help the warm smile that spread across his face at the suggestion, loving how they took care of him after their most intense fucking sessions. “Sounds fantastic.”

“Okay, I’ll go do that,” Sam said as he left the room, giving Dean’s face a final loving stroke before he left Cas to tend to Dean’s sore cheeks.

“How badly does it hurt, Dean?” Cas asked, tenderly wiping the blood away with the cloth as he tried to sooth the red welts on Dean’s skin.

“Not too bad.” He was understating it, but he always did when it came to any kind of injury. Cas knew as much.

“Would you like me to heal you?”

Dean considered the offer, but he thought he liked having Sam’s marks on his skin for a little while longer. “No, it’s okay.”

“Are you sure?”

Dean nodded.

“Okay, well if you change your mind just let me know,” Cas assured him, pressing a kiss against the bare skin of Dean’s back before proceeding to rub antiseptic cream over his reddened ass cheeks.

Once Dean was feeling more comfortable, Cas dressed himself in pajamas and then wrapped Dean in a blanket to bring him through to the living room where Sam had laid out the drinks for them. He'd also brought pie, the sight of which brought a smile to Dean's face. They let Dean pick the movie – he opted for _The Avengers_ – before the three of them settled down on the couch and snuggled up against each other. Dean settled himself down between Cas and Sam, losing himself in the warmth emanating from the pair of them as he wondered if there was anything else they could be planning for him that would ever top this.

 


	7. Chapter 7

**Summary for the Chapter:**

> Kink: enemas, light bondage

**Notes for the Chapter:**

> I'm sorry this update took so long to get posted! I got really distracted writing other stuff, but rest assured, I'm still trying to work through my tour of as many kinks as possible featuring Sam, Dean and Cas. I hope people enjoy the new chapter, since I know it was a long time coming.

A warm haze had settled on Dean's mind, calling him back into the bliss of peaceful sleep even as he felt his body awakening. He was gradually becoming aware of his surroundings again, feeling comfortable and calm as he processed that he was still naked and wrapped only in a soft blanket, and judging from the feel of the gently yielding surface beneath him, he was on the couch rather than the bed. It occurred to him that he couldn't detect Sam or Cas' presence anywhere, and wanting to know where they were, he blinked his eyes open and looked around.

Casting his gaze about, he saw that he was alone in the living room, and was tempted to go and find Sam (since he thought he was due his morning shower anyway) but before he could get up he saw Sam's tall frame emerging from the door to the hallway, wearing a bathrobe as he walked back into the room clutching a mug of coffee and a plate of toast. "Morning," he greeted Dean with a smile, seeing that he was awake. "How are you feeling?"

"Good," Dean answered, again downplaying the soreness on his buttocks. "I think you tired me out yesterday."

"I hope we did," Sam said, setting his coffee and toast down on the table. "We wanted to move you to the bedroom when we saw you fall asleep, but you just looked too peaceful to disturb. How's your ass? Not hurting too much?"

Dean shook his head. "Nothing I can't handle."

"Good," Sam replied with a smile as he sat himself down on the couch beside Dean, who wriggled a little to make room. "If you're not feeling too sore, Cas and I have a treat for you later."

That caused a flutter of excitement in Dean's stomach as he wondered what it could be, and as Sam saw the look on his face, his grin turned into a smirk.

"Now Dean, if you want that treat, you don't get to have breakfast today, understand?"

Dean didn't understand what this was all about, but he nodded obediently. Sam looked pleased.

"Okay then," Sam said, picking up his coffee and finishing it before setting the mug back down. "Cas and I have already planned what we're going to do with you today. We're going to leave your cage off a little bit longer and I'll put your butt plug in later. You and I are going to take a shower now, and then we'll go find Cas, alright?"

Dean nodded again, eagerly anticipating what it was that they wanted to do. They'd not put the cage back on while he was sleeping and his cock felt good to be free, but it was already itching for the attention it was normally lathered with whenever it was out of the cage. After a moment, it seemed that Sam might be about to give it some.

"Right then, Dean. First, take that blanket off and spread your legs for me. I want to have a look at your cock."

Grinning eagerly, Dean obliged, and he let the blanket fall away from his naked form as he opened his legs as wide as possible. Sam stared down at the sight between his thighs approvingly. Dean's cock was soft, sitting on top of his ball sac as it hung down between his legs, but it was just beginning to harden from excitement.

"Very nice, Dean," Sam commented. "Now can I have a quick suck of it for breakfast?"

He looked expectantly at Dean for an answer, and Dean swallowed. He was sure this was a test. Sam had sucked him last night, so he thought it must be Cas' turn today, and he didn't want to misbehave. As much as he would love to feel Sam's mouth on his cock right now, he wanted his surprise treat more, which he wouldn’t get if he broke the rules. Dean shook his head. "No. Cas owns my cock today."

"But Cas isn't here, Dean. We don't have to tell him."

Dean shook his head again, determined not to give into the bait for punishment.

Sam had a devilish glint in his eyes. "Don't you want to be naughty, Dean?"

"No. I want to be good."

There was a pause, and Dean wondered for a moment if that was the right answer, then Sam's expression turned into a warm smile. "You _are_ being good, aren't you?" he said proudly, leaning in to kiss Dean's forehead. "Well done, Dean. I'm proud of you for resisting. Now, let's go take that shower."

He patted Dean's cock as he leaned back again, and Dean smiled contently as Sam got up to lead him through to the bathroom.

After a good scrubbing down during which Sam had given Dean a very soapy, bubbly handjob, Sam dried each of them off before applying some cream to the remaining welts in Dean's butt cheeks. They then went to the bedroom so that Sam could get dressed, and Sam fitted Dean's collar and leash back on before giving it a tug.

"Alright, let's go find Cas," he said as he began to lead them back through the bunker. Dean was a little surprised when instead of heading for Cas' room or the dungeon, Sam took him towards the infirmary. As he was led inside, Dean felt his heart racing with excitement. If they were going to the infirmary, that probably meant Cas and Sam were going to play doctor with him, and after years of watching _Dr Sexy, MD_ that kink had become one of Dean's favorites. His cock twitched eagerly as Sam pulled him into the room and shut the door.

Cas was waiting for them, and he cast an appraising glance over Dean's naked form as they entered. "Good morning, Dean. I see Sam has got you nice and cleaned up," he said with a grin. "Now then, we thought it was about time to give you a proper clean up on the inside as well. So, we've brought you in here and we’re going to put some nice salty water up that tight little asshole of yours. How does that sound?"

As Dean realized they were going to give him an enema, his stomach began to perform excited somersaults. It was something they’d only done once or twice before, but Dean loved it. “Yes, please, Cas. I’d like it if you cleaned me out,” he said eagerly, wanting to please them so that they’d make it as fun as possible.

Sam grinned at how needy and obedient Dean was. “Dirty little whore like you, you must be filthy. I bet you’ve still got some come left up there, haven’t you?” he said, giving Dean’s ass a light slap and causing him to wince. “You need a good cleaning out. Right then, let’s get started.”

He handed Dean’s leash over to Cas, who began to pull him over towards the examination table while Sam went to prepare the enema. The table had been equipped with a pair of gynecological stirrups, and Cas ordered Dean to lie down on it before tying his leash to one of the table legs. “Feet up,” Cas instructed, “And spread your legs nice and wide so we can get to your hole.”

Dean did as instructed, swinging his ankles up into the stirrups, and then Cas went to stand between his wide open thighs. Dean’s cock was still in the process of hardening, and Cas moved to stroke it once or twice so that it stood up stiffly and bent back towards Dean’s abdomen. “Be a good little slut for us and keep that hard, Dean,” Cas said. “We need it out of the way. Now then…” He leaned in closer to study Dean’s hole, and then reached up a finger to gently poke at it. The pucker clenched and spasmed at his touch, and Cas nodded in satisfaction. “That looks nice and tight, Dean. It should be good for keeping all that water inside you.”

Dean hoped it would be. His cock throbbed and he was growing impatient for them to get on with things, but then he saw Sam join Cas between his legs. Sam spent a moment or two admiring the view, loving the angle that so perfectly displayed Dean’s gorgeous cock and balls and his pretty pink hole, and then he got down to business. Cas moved out of the way as Sam produced the nozzle and then leaned in to insert it, and Dean gasped as he felt the slicked up tube being pushed into his ass. It went in quite a way, and Sam smirked as he finally got it inserted as far as necessary. “There’s so much space up there, Dean. My, you are a slut.”

The insults always turned Dean on and he blushed, feeling his cock twitch as it dripped out precome onto his stomach. Cas leaned over him to lick it up, and then swiped his tongue over Dean’s tip on the way back up. The sensation caused Dean to whimper. “Can’t even stop yourself making a mess now, can you, you dirty whore?” Cas taunted. “Sam, I think you need to get on with cleaning him.”

“Yes, I think I do,” Sam said, adjusting the tube coming from Dean’s ass as he picked up the first bag he'd prepared of salt water solution. “Now then, Dean, let’s give your insides a good wash.” He raised the bag to let the enema flow inside, and Dean gasped and moaned as he felt the cool water steadily entering him. His belly began to bloat, and Cas placed a hand down against it and gave it a rub as he felt Dean fill. Sam went steadily, and it took a minute or two to empty the first bag inside Dean. Once done, Dean let out a whine, feeling the chill weight of the water in his gut. He wanted more.

“That’s half a liter,” Sam said with a grin. “But that isn’t going to be enough to clean you properly. I’m going to give you more.” He began to administer the second bag, and Dean sighed as he felt his belly swell even further. He knew it would reach a point of being uncomfortable, but that only made him enjoy it all the more.

Cas, meanwhile, had removed his hand from Dean’s abdomen and disappeared from sight for a moment or two. When he returned, Dean felt a thrill as he saw that he’d acquired a stethoscope.

“I want to listen to what’s going on inside you, Dean,” Cas said as he fitted in the earpieces, looking very enthusiastic about what he was about to do. “Now then, this may be a bit cold…”

Dean braced himself for the chill as Cas settled the end of the stethoscope on his stomach, the coolness of the metal matching the temperature of the water inside him. Cas’ other hand settled on Dean’s abdomen and began to caress his increasingly rounded belly, while the angel listened to the sound of the water flowing in Dean’s gut. Dean could feel it gurgling inside him, and Cas seemed to be enjoying the sound. After a few moments listening, he lifted his hand and then delivered a firm slap to Dean’s swollen stomach. Dean yelped as the action caused the water to slosh around uncomfortably inside him, and Cas chuckled. “You’re getting full, Dean, but I can hear there’s room for more in there. You won’t get clean unless we fill you right up.”

Sam finished the second bag and then began to administer the third, and Cas continued to move the stethoscope across Dean’s stomach as he listened to the flow of the water. Although it was growing more uncomfortable, Dean found his was completely enjoying this. Having Sam pump the water into him while Cas listened was a pleasingly kinky scenario, and the sensation of the liquid moving inside him was amazing.

After about a minute, Cas began to move the end of the stethoscope further up Dean’s abdomen towards his chest. “I want to have a listen to your heart now,” the angel explained. “And see how it’s coping. Breathe deeply for me, Dean.” Then he set the chestpiece down over Dean’s ribs.

The flat percussion of Dean’s heart filled Cas’ ears, thumping rapidly, and the angel sighed in satisfaction. Hearing Dean’s excitement and pleasure in his heartbeat was immensely gratifying, and Cas looked down at Dean’s face for an extra gauge of how much Dean was enjoying it. Dean stared back up at him opened mouthed as he tried to keep up the deep breaths, looking completely thrilled, although his gut was becoming so full he felt like there wasn’t much space left in his chest for air. As their eyes met, a delightful bloom of pink spread across Dean’s cheeks from his embarrassment at how much he liked this.

Cas licked his lips. “You should hear how excited he is, Sam,” the angel said, talking to Sam but keeping his eyes fixed on Dean. “His heart’s getting all fluttery. He loves having you fill him up.”

Sam raised his head then from staring at the nozzle in Dean’s asshole to look at his face. “Getting turned on by me cleaning you, Dean? Is it making your heart beat hard? I think I want a listen.” He straightened up to accept the stethoscope from Cas, who offered him the earpieces, and then he positioned the end back against Dean’s chest. Dean felt his heart speeding up just from having them both listen to it. There was no way to hide how much he delighted in this kind of debauchery when the banging of his heart clearly gave it away, and Dean saw Sam grin with pleasure at the sound of his excitement. “Listen to you getting all worked up,” Sam remarked, “You just can’t keep yourself under control, can you? But don’t worry, Dean. We won’t tell anyone what a slut you are or that you like such filthy things. Your heartbeat’s just for us, and only we know that having your ass filled up makes your heart race.”

Sam was grinning wickedly down at him, and Dean felt his cock throb and dribble out even more precome onto his bulging belly. He felt like he was stuffed almost to bursting point now, and his stomach was starting to cramp from the coldness of the water, but Sam wasn’t done.

“Now, that’s three liters, Dean. Do you have space for more?” Sam shifted the stethoscope back onto Dean’s stomach, tapping the bulge with his fingers to hear how the water sloshed and rumbled inside him, and he nodded as he heard the faint hollow noise indicating there was still some room left. “I think you do. Would you like me to give you another bag and make you nice and full?”

Dean already felt full, full enough at least to be uncomfortable, but he didn’t want to disappoint either Cas or Sam. He was polite and almost pleading in his reply. “Yes please, Sammy. I’m a dirty slut and I need you to make me all full so I can be clean.”

Sam smiled. “Good boy,” he said, leaning down to kiss Dean’s cheek, and then he set the stethoscope to one side and began to empty the final bag into him. Dean moaned in discomfort, although he tried his best to stay still.

As the last of the liquid entered Dean, Cas placed both his hands on Dean’s swollen belly and began to rub all over it as he delighted from the feel of Dean being so round and bloated. “Well done, Dean, for taking it all,” he praised, and then bent down to press a kiss on Dean’s stomach. He followed it by a few more, moving towards Dean’s navel so that he had to nudge Dean’s cock out of the way with his nose. “You have a lovely little belly. Having all this water inside you makes you so big so that there’s more of you for us to share. I hope we can keep you like this for a bit.”

As he pulled away after the final kiss, Dean saw that he was grinning, as was Sam. The younger Winchester smiled down at his brother, loving the sight of Dean all filled up with his cute little bump of a belly and his legs still spread so that Sam could see the tube protruding from his asshole. Dean’s cock was also still hard and leaking, looking like it was stuffed just as full as his stomach, and Sam was delighted by it. “Right then, Dean,” he said happily. “I’m going to take the nozzle out now, and you’re going to make sure you hold all that water up there. Then, I’m going to put this in,” – he held up an inflatable butt plug for Dean to see – “And we’re going to leave you for a bit while your insides get all nice and cleaned out.”

He proceeded to begin to remove the tube, and Dean grinned as he once again felt fingers probing and playing with his asshole before new things would be inserted. He tried his best not to let his channel open so that he kept every drop of water inside him, but as Sam’s fingers poked at his rim before inserting the butt plug, a small amount leaked out. “Don’t worry, Dean, that was my fault,” Sam reassured him. “You’re doing very well.” Then, with the plug in all the way, Sam begin to inflate it.

Dean gasped. He already felt stuffed to the brim, but as the plug expanded it compacted all the fluid inside his gut even more, making his belly feel tight and ready to burst. Cas’ hands had returned to it to give it soothing rubs, but the additional pressure from his firm touch only caused more discomfort. As the plug filled completely, Dean felt it blocking his entrance so tightly that it would be impossible for anything to leak out. He was finally how they wanted him.

Cas and Sam stepped away, staring down admiringly at the sight of Dean on the table: plugged up, bloated, cock throbbing, and looking as devastatingly hot as anything they’d ever seen.

“I think leaving him like that for an hour or two should be long enough, don’t you, Sam?” Cas said, “We still need time to give him his treat later.”

As Dean heard that, his cock twitched again. He was hoping one of them might give it some attention soon, but he doubted that they would and he didn’t want to get into trouble for touching it himself.

“I think that should be long enough,” Sam agreed, “But I don’t think we can trust him enough to leave him by himself. He might try touching his pretty cock and making himself come if we don’t tie him up. I don’t think he’s quite learned yet that his dick his ours.”

“Quite right,” said Cas, taking a step back towards the table, and Dean felt a rush of excitement as he realized what they were going to do. “Dean, I’m afraid we’re going to have to restrain you. I know you’re trying very hard to be good for us, but the thing is, you’re a slut, and we know what sluts are like. We can’t trust you to leave your cock alone.”

Cas was standing on Dean’s right while Sam had moved to Dean’s left, and they both began fastening Dean down to the table using the straps it had been equipped with. Dean squirmed and wriggled, making sure to yell in the hopes that they would tie him down tighter, and it seemed to work as his arms were strapped to his sides as firmly as was possible without it hurting. He was left breathing heavily from the brief struggle, and then he felt another thrill as they proceeded to secure his feet into the stirrups and spread them as wide apart as possible. Still his cock was rock hard and leaking, and he knew it wouldn’t be getting any relief any time soon. He thought it might even have been less uncomfortable if they’d put the cage on to stop him getting hard in the first place, but that was of course why they’d left it off.

“Alright then, Dean, we’ll be back in an hour to get you all flushed out,” Cas said with a grin. “And if you’re a very good boy in the meantime and don’t make any noise, we’ll make sure you get your treat.”

As they left the room, Dean felt his head spinning with a mix of intense pleasure and frustration from the state he’d been left in, and even more excitedly curious as to what his treat would be.


	8. Chapter 8

**Summary for the Chapter:**

> Kinks: more enemas

**Notes for the Chapter:**

> Sorry it's a bit short, but I'm trying to get back into a good update schedule and I didn't want to leave it too long again. I think this is enough of a teaser for next time.

It didn't take long before Dean was growing uncomfortable and itching for them to come back. He could feel the water swirling round inside him, cold and heavy, and he was starting to wish for release. Painful cramps had begun to clench through his abdomen, and it was a fight to not moan and be good and quiet like they'd asked.

His cock still managed to put up a good show, and it took several minutes for it to go down, unfulfilled but realising it wouldn't be getting any attention as Dean's discomfort killed his arousal. He just wanted Cas and Sam to come back and play with him again. Whatever they did to him, as long as it was them doing it, then it was Dean's favorite thing in the world. He wasn't a cockwhore, and he knew their taunts and insults were just for the purpose of turning him on, but attention whore? Yeah, he was that. Whether they were putting their dicks in him or other things, Dean was happy as long as he was the centre of their focus. Maybe he was spoiled, having two of them to play with his body, but he sure didn't feel bad about it. It just made it more of a challenge to be good and not whine whenever they left him on his own.

He held out for the first hour, keeping his whimpers quiet whenever they left him at all, but it still took a little longer than that for Sam and Cas to return. It was closer to two hours when Dean finally heard the door opening again, and then both of them were stood looking down at him and admiring the sight of his naked body.

Cas gave a nod of approval. "Good," he said, patting Dean's belly. "I think that should be enough to get you freshened up a bit.

Sam then went to position himself between Dean's legs, and Cas cupped Dean's limp cock to hold it out of Sam's way. "Okay Dean, I'm going to take the plug out now," Sam said, "But I need you to hold onto the water a bit longer. Keep your asshole nice and tight, because you're going to take yourself to the bathroom and empty yourself out fully. Make sure there's plenty of space for us up there, okay? And if you can do it without spilling a drop on the way, we might let you have a bit of breakfast then we'll give you your treat. Do you understand, Dean?"

Dean nodded eagerly. "Yes, Sammy."

"Good boy," Sam said with a smile as he rubbed the inside of Dean's thighs, and then his fingers returned to Dean's hole as he began to deflate the plug.

Dean sighed as he felt the intense pressure inside him easing slightly, and then gasped sharply again as Sam's fingers began to stretch at his rim to ease the toy out. A small dribble of fluid escaped as the plug slid out of him, and Dean bit his lip, but Sam was reassuring. "Don't worry, Dean. That happens. Just make sure you hold onto the rest of it." He set the plug to one side for cleaning and then stood up, watching the strain on Dean's face as he fought to keep his hole tightly clenched. Cas had placed both hands on Dean's belly and was pressing down firmly, deliberately making it more difficult for him.

"Now then, Dean," Sam continued, "We're going to untie you now and you're going to take yourself to the bathroom to get emptied. It's just down the hallway, so we're not asking you to go far, but we don't expect to have to clean up any leaks from you. Understand?"

Dean nodded.

"Alright," Cas took over as they both begin to unfasten his restraints. "When you're done, come and find us in the kitchen, okay? And we'll decide if you've done a good enough job. Now off you go."

As Dean's restraints fell away, they both stepped back and stood watching him expectantly. Neither offered him any assistance in getting up, so he was forced to awkwardly swing his legs out of the stirrups and attempt to clamber off the table on his own. He managed it, although the process of standing put the most strain on his hole as gravity tugged at the water inside him. Once on his feet, he didn't know how to move without disturbing the liquid even more, and his channel felt immensely uncomfortable as he tried to force it to stay shut. It was all he could do to just waddle to the door, cheeks burning with embarrassment, and he hoped they were both enjoying how ridiculous he looked.

Once he'd reached the hallway, he found it was easier if he got to his knees and crawled. The angle made his belly bulge out even more towards the floor, like a little pouch full of water, but there was less pressure to hold it in.

Sam and Cas watched him, enjoying the view of his cock and balls swinging between his legs while the dome of his belly protruded beneath him. His ass was perfectly on display for them, still a little red from last night, but after the play around Sam had just had with Dean's hole, that didn't seem to be bothering him anymore.

As Dean finally made it to the bathroom door and crawled inside, Sam bit his lip trying not to laugh. It was hot, but it was funny too. Dean had such a beautiful body that they could do such absurd things with.

Cas was amused too, but was hiding it better. "Don't let him hear you," he said quietly. "He'll get upset, then he'll be mad with you later."

Sam was still smirking. "He won't. Maybe a little, but he loves it really. Sometimes I think we don't humiliate him enough."

Cas' lips twitched to form an expression similar to Sam's own. "Let's get on with rectifying that, then. We've got all day."


	9. Chapter 9

**Summary for the Chapter:**

> Kinks: speculums, rimming, and believe it or not, even more enemas, but this time with a twist

It came as an immense relief for Dean when he finally let the water out, releasing all the pressure inside him and feeling pleased with himself for not spilling any before he reached the toilet. That surely meant he'd be getting his treat now. Sam and Cas must be pleased with him, he hoped. They'd trusted him enough to go to the bathroom by himself with his cock still uncaged, and he was determined not to let them down by touching it.

Instead, he fought the urge to get himself off and went straight to the kitchen as instructed. Sam and Cas were waiting for him, and Cas appeared to be in the process of making coffee for them, but they both smiled as he appeared in the doorway.

"All emptied out, Dean?" Sam asked.

Dean nodded.

"And how does it feel?"

"My ass feels very clean now. Thank you for washing me out, Sammy."

Sam gave a pleased grin. "Alright. Come here, then," he said as he stood up. Cas was still doing something with the coffee machine. "Bend over the table, Dean. I'm going to have a look at your hole and see how good a job you've done."

Obediently, Dean crossed to the table and bent down over it, offering up his ass for inspection. His cock rubbed against the table's edge as he felt himself getting hard again, and he wished they'd put the cage back on. It was frustrating when he kept getting erections they wouldn't take care of.

"Okay, Dean," Sam said as he carefully pried apart Dean's cheeks. "That's looking nice and tight. Let's see how it feels inside." A finger gently rubbed over his hole and then pushed into him, and Dean gasped. "That already feels much cleaner," Sam said, pleased, as he pulled his finger away again. A moment later, and Dean felt a warm moistness against his hole as Sam's mouth closed over it. A hot tongue lapped all the way around his rim and then pushed into his opening, and Dean yelped and squirmed. It felt fucking amazing.

Cas, meanwhile had crossed round to the opposite side of the table and now stood grinning at Dean. "Enjoying that?"

Dean nodded breathlessly as Sam continued to rim him.

Cas smirked. "How does he taste, Sam?"

"Nice and fresh," Sam answered, pulling his mouth back and licking his lips. "But I think we need to open him up a bit more to see how clean he is inside.'

Dean hadn't quite been following what was going on between them until Cas produced an object from beneath the table, and then set it down for him to see. Dean's cock twitched and his heart picked up pace as he saw it was a speculum. "Perhaps we'll be needing this?" Cas said, grinning wickedly, and Dean felt a thrill as he slid the instrument across the table to Sam.

Sam picked it up, and the next thing Dean knew was the feel of the cold metal prongs being inserted into his ass. "Agh...fuck!" he cried out, unable to contain himself.

Cas tutted. "Watch your tongue, Dean. You've been such a good boy for us, don't spoil it now. Be quiet while Sam's inspecting you."

Dean gritted his teeth and nodded. His cock was rock hard and throbbing now, and he felt precome dribble out and leak onto the table as he rubbed against it in his desperation for more friction. He hoped that wouldn't get him in trouble, but Cas and Sam were both too fixated on his ass to notice.

As Sam jacked the speculum open, Dean bit his lip as he tried his hardest not to make any noise and keep his hips still. He could feel his muscles clenching tightly around the intrusion, and he tried to relax to make Sam's job easier. Cas was still stood off to his side, and he could see the angel grinning as he watched Sam. "What does he look like up there, Sam?"

"He's looking very pink and clean, Cas, but it's a bit hard to see. Can you hand me the penlight?"

Cas flashed Dean a grin as he produced a small penlight from his pocket and handed it to Sam, who proceeded to shine it into Dean's gaping hole. Dean felt dizzy with arousal and he was desperate for Sam to put his fingers or just _something_ inside him, or at least for one of them to rub his neglected cock if they weren't going to put anything more than cool air up his ass.

"Everything's looking very nice up here, Dean," Sam announced, sounding pleased. 'I'm just going to have a feel." It was at that point he finally thrust his fingers into Dean and started probing and massaging Dean's walls, and Dean let out a shuddering gasp. Cas was still stood grinning as he watched them, a noticeable bulge in his pants that he was rubbing absently through the material.

There was enough space inside Dean for Sam to insert four fingers all in one go, and as he brushed his middle finger over the bump of Dean's prostate, Dean almost came right there. It was even more difficult to hold off orgasm when he didn't have permission to come than it had been to hold the enema all that time. He was desperate to be allowed to finish, but they weren't done with him.

"Come and have a look at this, Cas," Sam said as he pulled his fingers out, and then Cas walked round the back of Dean to join him. "What do you think? Does he look clean enough to you?"

Cas took the flashlight off of Sam and shone it up Dean's ass. The space inside Dean's body was gorgeously pink and moist, the walls looking soft and tempting, but he was otherwise empty and clean. There was just the little bump of Dean's prostate that stood out a few inches down his channel, and Cas was tempted to reach in and give it a poke, but he didn't want to finish Dean yet when they had more plans for him. "He looks good and clean to me," Cas said, straightening up and handing the penlight back to Sam. "You'd never know what a whore he is. I think we can get him closed up."

Dean let out a whine then as Sam began to close the speculum back up. "Good boy, Dean," he praised as he slid the prongs back out, so that Dean's hole tightened again to just a narrow but no less enticing opening. "Now then, did we promise you some breakfast as a reward? And a treat?"

Dean was still bent awkwardly over the table, but he swallowed excitedly and nodded. Finally, he hoped, he'd be finding out what the treat was.

In his left field of vision, Cas suddenly reappeared, wearing a smirk. "Okay then, Dean. We're going to let you have some coffee," he said by way of explaining what he'd been doing earlier, then his grin broadened. "But you won't be drinking it."

Dean only had a moment to be confused before he felt Sam's hand between his shoulder blades, pushing him down hard against the table, and then something else was being inserted into his ass. He yelped in surprise. He most definitely wasn't complaining, but he hadn't expected them to put something back into him so soon.

"Now that we've got you cleaned out with some fresh water," Cas explained, leaning over the table to bring his face closer to Dean's. "We're going to put something more interesting up there. It should be a bit more comfortable for you, Dean, since we've kept it warm."

Dean stared across at him with a dazed look as he felt Sam push the nozzle further into his ass. After the discomfort of the last enema, he hadn't thought he'd feel this pleased to be getting another one straight after, but he was. It was definitely a new experience for him when they were using black coffee instead of water, and that thrilled him. He couldn't see exactly what Sam was doing, but he heard the faint noise of bags of fluid being prepared before a warm liquid began to flow into him.

It was already more comfortable than last time, the temperature more closely matched to that of his body and causing a pleasant warmth to spread through his insides. There was also an unexpected but not unwelcome tingling in his gut, and he found he liked this even more.

"We're going for the full four liters again, Dean," Sam said as he dispensed the liquid. "And you're going to hold it long enough to absorb all the caffeine and everything else from it."

Dean nodded enthusiastically. He loved this and he wanted to seem grateful. "Yes, Sammy. Thank you, Sammy. Thank you, Cas."

Cas smiled warmly at him across the table, reaching out to stroke his hair. "You've been such a good boy, Dean. You've earned your treat."

The praise filled Dean with joy, even though he was growing increasingly frustrated with prolonged anticipation and his balls were beginning to ache. He hoped they'd let him come soon.

Once he was pumped full again, belly bulging against the table, Sam inserted another butt plug and let it inflate until Dean was completely blocked up. "Okay, you can straighten up now, Dean," he said, stroking the sides of Dean's ass from his hips to his thighs, and Dean did as instructed. Now his stuffed and leaking cock was visible for both of them to see, and they both looked down at it. It seemed they were enjoying the view, but neither showed any inclination to touch it. A faint whine sounded in Dean's throat. He couldn't take this anymore.

"Please, Sammy," he whispered nervously, resorting to begging. "Thank you so much for filling up my ass, but please may I be allowed to come?"

Sam smirked. "I don't know, Dean. I think you should ask Cas."

Dean's eyes flickered over to the angel, who was watching him with a hungry gaze. "Please can I come, Cas?"

"And why would I let you do that, Dean? I like looking at your cock hard," Cas answered, deliberately tormenting him.

"Please, Cas. My balls hurt and I'll get hard for you again as soon as I can."

The angel seemed to consider it for a moment. "Well, you _are_ begging very beautifully for me, Dean, and you're being so polite. How would you like to come?"

Feeling relieved, Dean said quietly. "I'd like you to touch my cock, please, if that's okay?"

Dean thought Cas had been about to agree, but then the angel seemed to have second thoughts. "We promised you a treat, didn't we, Dean? Well, you can either come now, or you can have your treat and come later. Which is it going to be?"

That was an infuriating ultimatum, but Dean knew he couldn't turn down finding out what the treat was. "I'd like the treat, please. I'll come later," he answered meekly, hiding his disappointment.

Cas smiled. "Good boy," he said, crossing to Dean and kissing his cheek. "Now for your treat, we're going to take you out. How would you like that?"

Dean's eyes flickered from Cas to Sam, wondering what exactly what they meant by that. "You mean...in public?" There was clearly an aspect to this that they weren't yet revealing, and that excited him all the more.

"Yes, Dean," Sam answered. "We thought we'd take you out for lunch, since it's been a while since you've left the bunker. We'll be a bit sad to see you get dressed again, but it'll be worth it to make you happy. And don't worry, we'll still have control of everything underneath."

There was a wicked glint in his eye as he cast his gaze up and down Dean's body, one hand gently caressing his rear. Dean's cock throbbed harder.

"We don't want you embarrassing yourself, Dean," Cas said, his hand joining Sam's to stroke Dean's ass. "So of course we can't take you out without getting you properly plugged up first. We need to make sure you don't make a mess."

Dean's stomach was squirming with excitement, and he could swear the warm liquid inside him had formed some kind of whirlpool.

"I've got your ass nicely plugged, but we need to take care of your other holes," Sam said, "And make sure you're secure. So, we've bought you a nice surprise to help with that. Would you like to see?"

Dean nodded eagerly, his breathing coming quick and shallow. The thought of going out in public with the enema and butt plug still inside him was terrifying, but also such a turn on. And, it seemed, they were about to do even more. If they were about to put something in his cock, Dean couldn't wait.

"Right then," Cas said, pulling out a strip of material from his pocket. "It's a surprise, so close your eyes."

As Dean obeyed, Cas fastened the blindfold into place to ensure no peeking, and then Sam reattached the leash to Dean's collar in order to lead him through the bunker to where his surprise waited.

**Notes for the Chapter:**

> When I started this fic, I promised myself that the relationship I portrayed had to be safe, sane, consensual and loving (no matter how unrealistic it gets) but I'll be the first to admit I'm taking advantage of the fictional setting so I can play on Cas' healing powers if I need to. I'm not at all convinced that Dean holding a coffee enema for as long as I intend for him to hold it for is actually safe, but if it's a one off thing, I'll roll with it anyway. I'm not exactly trying to be realistic. There are therefore several inaccurate and not-possible-in-real-life aspects to this fic, but let's be real here, accuracy and realism aren't why people are reading this, right?


	10. Chapter 10

**Summary for the Chapter:**

> Kinks: harnesses, catheters, cock cages, butt plugs, nipple clamps

The stale chill in the air told Dean they were back in the dungeon again. The concrete floor was cold beneath his bare feet as he was led across it, feeling the leather collar press into his throat with each insistent tug on the leash. Sam almost seemed as excited as Dean was, judging from how keenly he was pulling Dean along. After they’d gone a few paces, Dean heard the door slide shut behind them and they came to a stop.

“That’s far enough, Dean,” Sam said, “Now are you ready to see what your present is?”

Dean nodded. “Yes, please.”

In response to his answer, Cas began to untie the blindfold and slide it off, and then Dean heard the angel’s voice in his ear. “Open your eyes.”

Dean did. His stomach did a backwards somersault as he saw what was laid out in front of him.

He was standing in front of a metal table, which was fully body length and equipped with straps, but although that was exciting in itself, it wasn’t what his attention was drawn to. Laid out upon the table was a leather harness, equipped with multiple straps designed to brace his body in various places, but most noticeably for the region between his legs. It had an in-built cock cage, far more imposing looking that his regular one, that was almost a solid metal tube with just a few holes for ventilation, and with an adjustable ring and straps to cradle his balls. Laid out next to the device was a plastic tube that Dean recognised as a catheter, a pair of nipple clamps, and a syringe that appeared to be pre-filled with clear fluid. The sight made him feel dizzy.

“Is this for me?” he asked, feeling giddy with excitement.

“It’s all for you,” Cas replied, grinning as he watched Dean’s eyes light up. “It’s something so you feel nice and secure when we take you out and you know we’ve got your body under our control.”

“Thank you so much,” Dean breathed, wanting to sound grateful even as his cock throbbed uncomfortably. At least now they were going to have to handle it if they wanted to put the harness on.

“Now then, Dean, we’re going to put it on for you, starting with this,” Sam said, picking up the catheter, but then he gave a disapproving glance down at Dean’s dick. “But it won’t fit properly with your cock in that state. What’s to be done about that?”

Dean swallowed down a whimper. _Please let them make me come…_

As if reading Dean’s thoughts, Cas sighed. “I suppose we’re going to have to get you off, aren’t we, you slut?” he said, feigning irritation. “Now Dean, I’m only going to let you come because you were good and turned it down earlier, okay? Otherwise I’d use my powers to make you go soft again. Now then, let’s see to your dick…”

At long last, he reached down to close his fist tightly around Dean’s swollen member and give it a slow stroke, and Dean’s eyelids fluttered shut as he let out a delighted moan. “Thank you…” he murmured quietly, almost unable to speak as Cas picked up pace and started to jerk him roughly and impatiently. Dean was already so close to the edge that it only took a few quick pumps to finish him, and soon he was spilling himself onto his stomach and over Cas’ hand as his entire body convulsed with pleasure. Once the final shock had worn off and the last glob of come had spurted from his slit, he thought his knees might be about to give out from under him. Cas held him up, grinning at the blissfully dazed look on Dean’s face. “We’ve barely even got started and you’re already making a mess,” he remarked, but Sam had a cloth to hand and they quickly cleaned him down.

“Right, time to get this fitted,” Cas said as Sam handed the catheter over to him. “Sit on the edge of the table, Dean.”

Recovering quickly, Dean did as he was told, allowing his cock and balls to hang just off the side of the table as he opened his legs. It was a little uncomfortable to sit down with the plug protruding from his ass, but he managed to adjust himself to cope. Cas bent down between his knees, holding onto the catheter that Sam had helpfully attached a hose and bag to. “Okay, I’m going to put this in now, and if you’ve emptied yourself out properly, I’m expecting it to come out dry at first. If it turns out you’ve been holding some water in your bladder, Dean, Sam and I might change our minds and not take you out after all.”

He sounded stern, and Dean shook his head. “I haven’t, I promise.”

“Good,” Cas replied, “Let’s get on with it, then.” He gripped Dean’s soft dick in his hand and lifted it to look at the tip, before pinching the head and pulling down slightly in order to roll back Dean’s foreskin and widen his slit a little. “This may be uncomfortable,” he warned as he pressed the end of the catheter against Dean’s narrow hole and started to feed the tube into him.

Dean gasped. It was uncomfortable, but at the same time managed to be strangely pleasant. He’d had sounds inside him before and very much enjoyed them stretching out and stuffing his cock, but with the less rigid material this felt slightly different. The catheter was thick – more so than he thought a standard medical urethral catheter was supposed to be – and the further it slid down his shaft the more it hurt. As much as he was enjoying it, his eyes were starting to water, and then he heard Sam speaking to him as the younger Winchester came to stand close by. “It must be very painful for you, Dean. Would you like me to hold your hand?” His tone was sincere, not mocking.

Dean found the suggestion embarrassing, and he thought they were treating him like a child, but he also thought that he quite liked it. He nodded. “Yes please, Sammy.”

Sam’s fingers moved to interlace with Dean’s own, gripping on tightly and caressing Dean’s skin with his thumb as Dean squeezed his hand hard from the pain. “Shh…” Sam soothed. “You’re being so brave for us, Dean. We’re so proud.”

Dean felt a warm glow swell inside him from the praise while he simultaneously clenched his jaw in discomfort, and then at long last the end of the catheter curved into his bladder and the process of insertion was done. The bag on the end remained empty, and Cas smiled. “All dry. That’s a good boy, Dean,” the angel said as removed the bag and then replaced it with the nozzle of the syringe. “I’m just going to put a bit of water in there to moisten you up.” He pulled the plunger, and Dean gasped as he felt a rush of cool water flow down the tube into his bladder and added to the pressure inside him. “Now I’m going to put a cap on the end to stop any leaks.”

Dean watched as Cas pushed down a cap on the end of the tube protruding from his cock, thus placing the last of Dean’s ability to relieve himself entirely in Cas and Sam’s control. It was thrilling, albeit a little nerve-wracking. The angel then straightened up, grinning at Dean as he did so. “Alright, on your feet again, Dean. Time to get the harness fitted,” he ordered, and Dean obediently eased himself off the table. He wanted to do so more quickly in order to show his enthusiasm, but the discomfort all throughout his lower abdomen and pelvic region made it difficult to move with speed.

Once he was standing again, both Cas and Sam began to efficiently fit the harness to him, manhandling him where necessary if he failed to heed their instructions fast enough. They hitched up the straps around his thighs and hips, ensuring his cock was fitted into place before they could tighten the rest of it. It felt very strange to Dean to have his cock stuffed up from the inside while it was simultaneously being contained by something without, but he loved how intense the sensations were. There didn’t seem to be an inch of his dick inside or out that wasn’t subject to some form of pressure or touch.

The cage was tight fitting, and it was a slight challenge for Cas to slide the soft flesh of Dean’s dick comfortably into it, but he managed it so that the tube fitted right down to Dean’s balls without painfully squashing him. There was a hole in the tip that had specifically been designed to allow the end of the catheter to poke through, and the cap was secured in place by a pin attached to the harness that could be locked into position. That made it impossible for the catheter to slip or become misplaced, and also prevented Dean from being able to piss without the key to remove the cap. It was just one more level of control that Sam and Cas had over his organs.

After finishing with his cock, Cas started to secure Dean’s balls, pinching the ring tightly around them and shortening the straps so that they were pulled up close to Dean’s body. Dean whimpered slightly from how much the sensitive glands were being compressed, but he also felt good knowing that all this pain and discomfort he was enduring was for Sam and Cas. They’d be proud of him for it, and he knew that they’d show their gratitude with a reward if he earned it.

Following his balls, the next thing to be secured was his ass. There was a strap that slipped neatly into his crack and was fitted with another pin that attached to the butt plug Sam had already inserted. That, too, could be locked up, ensuring there was no way to remove the butt plug while the harness was in place. Sam fitted it in, and then went to adjust the strap around Dean’s waist, that was acting as a belt to hold everything else up. He pulled it tight against Dean’s swollen belly, causing Dean to moan in discomfort. “Is that too tight for you, Dean?” Sam asked, but Dean shook his head. No matter how much his stomach was cramping from feeling too tight or full, it was worth it just to have them touching him and paying so much attention to him like this. He was determined to endure it for them.

All of the main straps of the harness had been secured now, and were tightly fitted around Dean’s thighs, his hips, his buttocks, and between his legs, but there was still more that could be attached. It was at that point Sam picked up the nipple clamps, handing one to Cas as they both stood in front of Dean and picked a nipple each. Cas took the left and Sam took the right.

They both had different approaches to how they were going to get the little pink nubs to harden, and Dean felt the tightness around his cock increase with his blood flow as they both set to work. Cas used his mouth, leaning in and extending his tongue to swirl over the tiny peak until it stiffened and began to protrude enough for the clamp to be fixed in place. Sam, on the other hand, preferred to be more manual as he rubbed at Dean’s nipple with his fingertips, and then pinched and pulled at it so that it swelled and the tip raised itself further from Dean’s chest. Dean whimpered and squirmed as they both simultaneously fitted the clamps into place and began to tighten them.

“ _Fuck…_ ” he gasped out as the metal clamps squeezed his nipples enough to hurt, and he didn’t know if he’d be able to endure this for the amount of time they wanted him to. He hoped that after a few minutes his nipples would go numb, although given that they were particularly sensitive in regular circumstances, he thought that it might take a while.

Both Sam and Cas grinned at the sight of him squirming in discomfort, loving how his body responded to them. “Shh, Dean, it’s okay,” Cas whispered. “We have to do this to fit the harness on properly. We’re just going to attach these to the belt now.”

The nipple clamps were intended for use with the harness, and they had loops that straps could be fitted to so that they attached to the waistband. Sam and Cas began to fit the straps in place now, tightening them so that Dean’s nipples were persistently being tugged downwards, while they also attached other looser bands around Dean’s chest and over his shoulders to stop the clamps slipping or becoming misplaced. Once that was done, they made a few final adjustments to the straps, and then both stepped back to admire their work.

Dean looked positively delicious. His body was all bound and pinched and plugged in just the right places, with the belts of black leather pulled so tightly across his skin that they could see his soft flesh bulge slightly around the edges. That would leave some beautiful red marks later. The sight of him was utterly obscene and gorgeous, and they both loved it. The only way it could possibly be improved was if they added a gag and the bindings to keep his arms and legs locked up, but since they were taking him out in public, those would be saved for another time.

Dean himself was loving it just as much as they were. His body was so tightly contained while at the same time stuffed full to bursting point, and the conflicting pressures and forces acting on him were a perfect counterpoint to each other. He loved how the tightness of the belt was balanced perfectly by how much his stomach bulged resiliently and defiantly against it, mirroring how the thick tube inside his cock pushed his flesh closer against the metal tube confining it, making everything feel tighter. The weights on his genitals as well as his nipples were heavy and comforting, and everything about this felt so completely secure. He was entirely under Cas and Sam’s control.

The satisfied looks on both their faces were a reward for Dean in themselves, and he grinned as his cheeks flushed with thrilled embarrassment at how obscene he must look to them.

Cas licked his lips as he cast his eyes hungrily up and down Dean’s body. “There, we’ve got you properly plugged and secured now. How does it feel?”

“Fucking incredible,” Dean answered honestly, his voice low and raspy. They both grinned.

“You _look_ fucking incredible, Dean,” Sam said back. “Now, I’m sure you’ve realised there’s a lot more locks for us to share on this one. We’ve got keys for your cock, for the catheter, for your balls, for your butt plug, for the belt and for the connecting straps on the nipple clamps, if anything needs taking out or loosening. So, we’re going to divide these between us so that we share you equally.” He then held up two key fobs equipped with a series of tiny keys for Dean to see, before giving one to Cas. They both pocketed them, and Dean felt his heart do a nervous flip-flop in his chest. As much as he loved this, he couldn’t pretend there wasn’t something at least a little bit frightening about surrendering control of his body so completely.

“Right, now that we’ve got you looking all lovely like this, shall we go get you dressed before we take you out?” Cas suggested before picking up Dean’s leash again.

They led him up to the bedroom where they picked out some clothes for him, and then began by sliding a pair of boxer shorts up his legs to his hips. It was quite a tight fit for them over the belt and cage, and Cas patted the bulge of Dean’s cock once they had the underwear fitted in place, causing Dean to whine in frustration that he couldn’t feel it. They followed that up by ordering him to sit on the end of the bed while they slipped on a pair of socks, then they chose a pair of jeans for him and started to dress him properly.

It felt strange to Dean to be wearing clothes again after spending so long permanently naked and on display, but he was enjoying having Sam and Cas dress him. The thought of what he was hiding underneath his clothes made him feel deliciously filthy, and his head spun as he anticipated going out in public like this. The jeans were his own pair, and as the denim slid up his legs Dean began to feel a sense of familiarity again, but when it came to doing up the button, he puffed in discomfort as his bloated belly proved too large for it. Sam had to pinch him in quite tightly to get them to fasten, and then when he added the belt on top he notched that even tighter, drawing it in a couple of holes further than was necessary. Dean cried out as he felt an intense pressure against his hole, the liquid inside him being forced downwards, but the plug in his ass was inflated far too much to allow for leaks. Some of the coffee instead seemed to be pushed higher in his gut as a greater band of restriction was applied around his middle, and his breath hitched from the painful cramping. His heart was beating much too hard, feeling strained from all the internal pressure, but Dean was determined to endure it. Not matter how uncomfortable, intense, difficult or overwhelming this felt, he was more than happy to put up with it for as long as Sam and Cas wanted. There was a strange aspect to the pleasure center in his brain that allowed him to simultaneously find sensations like this unpleasant but also completely fucking amazing, and he was already hungry for more.

The t-shirt came after the jeans, and both Sam and Cas manoeuvred Dean’s arms through the sleeves and pulled it down over his head to put it on. The shape of the harness and nipple clamps were clearly visible through the thin material, but that would be disguised that with what came next. The overshirt they chose for him was one of Sam’s: red plaid and a little too large, but as they pulled it on and buttoned it up, it was loose enough to hide all the shapes of the devices they had fitted to him. Then came the shoes and jacket, which they put on for him to almost complete the illusion of Dean being completely ordinary, rather than their obedient little submissive who even now had his body bound up subject to their wishes.

Finally, the last thing to do was to remove Dean’s collar: as lovely as it was to see wrapped around that gorgeous throat, it wasn’t for public viewing. Once the leather band had been unfastened and pulled away, Cas and Sam stepped back once more to admire the view. “Well, look at you, Dean,” Sam said appraisingly. “I must say it’s a shame to hide that beautiful body of yours, but you look completely normal. No one could ever tell what a slut you are without having a good feel.” He reached forward to tug at a nipple clamp through Dean’s clothes, prompting a moan, and Sam smirked. “What do you think, Cas? Does he look passable to you?”

“I think so,” Cas replied, giving an approving nod. “He looks all set to go. Now Dean, shall we take you out for lunch?”

Dean nodded enthusiastically, delighting in the feel of the fabric on his skin and the leather straps pinching his body and the liquid stuffing his stomach full, so that his senses were completely overloaded as he anticipated what was about to come.

Cas flashed him a grin. “Lead the way, then. You’re going to have to get used to walking without a leash if we’re taking you out in public.”

Dean smiled back, enjoying the extra bit of responsibility he’d been trusted with as he picked up his feet and began to walk in the direction of the garage. He was, admittedly, terrified of going out in public like this, but the fear was only making it more thrilling and he knew already that whatever happened once they left the bunker, he was going to love it.


	11. Chapter 11

**Summary for the Chapter:**

> Kinks: basically, holding an enema while wearing a cock cage and a butt plug in a public place, and having the harness adjusted

**Notes for the Chapter:**

> I said I was going to get into a better update schedule and then I go and leave it without and update for ages, so I'm sorry. Things just kept getting in the way. This fic is also getting weirder and more extreme the longer it goes on, so I think the chapter after this (and maybe this one) may not appeal to some people and I wanted to warn you well in advance, but beyond that most of what I have planned is fluff piled on top of smut to compensate.
> 
> Update: I have rewritten this thanks to a commenter who pointed out there was a lot of problematic content this chapter. I do agree. I would 100% rather rewrite every word of this fic than just stick a warning on it and say that it's abusive, because that is not the kind of relationship I want to portray at all, so if I fuck up, I will fix it.

The car journey was almost unbearable for Dean. Sam was driving and Cas was in the passenger side while they’d put Dean in the back, leaving him relentlessly squirming in the seat although the discomfort persisted no matter which way he shifted himself. With the harness strapped tightly to him and squeezing the most sensitive parts of his body, there was no way to sit that wasn’t uncomfortable. He kept wriggling to try to find a way to alleviate the pressure, but there was no position that didn’t only worsen things for at least one part of his body.

His nipples still hurt. The pain hadn’t numbed, like he’d hoped, but the sharp pinching had at least faded to a dull ache. It was just one more sensation adding to the overload feeding into his brain, but intense though it was, so far, Dean thought he could endure this.

Enduring it while sitting still, however, was another matter.

“Stop squirming, Dean,” Sam reproached, noticing his motions in the rear view mirror. “We can’t take you out in public if you’re just going to fidget like that. What will people think?”

“Sorry, Sammy,” Dean apologised, immediately trying to still himself. He managed it somewhat, choosing to sit leaning forward so as to lift some of the pressure on the butt plug, although it increased the tightness around his waist.

In the end, it was over an hour before they pulled up into the parking lot of a diner for lunch. Dean knew there were other almost-identical restaurants nearer the bunker, but of course Cas and Sam would want to prolong his endurance ordeal in the back of the Impala for as long as possible. “Remember, Dean,” Cas said just as they were about to exit the car. “They don’t like serving sluts in these places, so you’re going to have to pretend you’re not a complete cockwhore, alright? Don’t let anyone suspect a thing.”

“Yes, Cas,” Dean answered with an obedient nod, horrified at the thought of anyone guessing what he had on under his clothes. He tried to act as normal as possible as the three of them exited the car and headed into the diner, although walking as opposed to waddling wasn't exactly easy.

They picked a booth by the window to sit in. Dean slid awkwardly onto the bench first, followed by Sam, while Cas took the seat opposite him. Dean found himself wondering what he was going to do when it came to eating. On the one hand, he'd had no breakfast and the thought of greasy diner burgers was usually enough to get his mouth watering, but he still felt so stuffed he didn't want to put a single thing more into his body. Sam spared him having to choose by leaning in close to his ear and whispering, "Dean, when they take your order you're getting a cheeseburger and a black coffee, okay? Just don't start eating it until we say so."

The thought of filling himself with even more coffee made Dean want to whimper, but he gave a discreet nod of acknowledgement.

When the waitress came over to them after a few minutes, Dean did as instructed. She took Sam and Cas' orders first - salad and a cheeseburger respectively - before getting to Dean, and he even managed a flirtatious grin at her to disguise what was going on. She was too busy smiling back to notice Sam's smirk.

"You into her, Dean?" Cas teased as she walked away again, and Dean felt Cas' foot under the table start nudging and his ankles.

He blushed despite himself. "Of course not. Just throwing her off the scent," he mumbled quietly.

Sam, meanwhile, had inched ever so slightly closer to him, and Dean felt a hand close around his thigh below the table. "That better be all it is," Sam growled quietly in his ear as he gave Dean's leg a possessive squeeze.

The gravel tone of his voice shot straight to Dean's dick, causing it to give an uncomfortable throb, but Dean's eyes still darted around in panic from fear that someone might have noticed. All the diner's other patrons, however, seemed completely oblivious.

He heard Sam chuckle slightly at his reaction. “How are you feeling, Dean?”

Sam had whispered it quietly, and Dean replied in a voice similarly faint. “Full.”

“You think you’ve got room for lunch?”

“Honestly? No.”

“Guess someone better do something about that, then.” Sam shot Cas a grin across the table. “You got the back keys, right?”

Cas held up the fob with his set of tiny keys attached to it and gave it a shake. “Yep.”

Dean gulped and squirmed a little in his seat. _Finally,_ he felt like saying as he realised he was going to at last get some relief.

Cas’ eyes flickered over to a spot somewhere behind Dean. “You want me to take you to the restroom? Keep in mind that there’s a man who’s just gone in. We could wait.”

Dean really didn’t want to wait, but he didn’t exactly want to do this in a stall with Cas while there was potentially somebody listening to everything. He bit his lip, looking uncertain whether he wanted to wait a minute or two or go straight away, but Cas seemed to notice. “Alright, you know what? We both go together someone will notice. Here.” He held out the keys to Dean, pinching one in particular between his thumb and forefinger.

Dean blinked at it, thinking he understood what it meant, but at the same time thinking he couldn’t be right.

“Just this once, you can take yourself,” Cas said. “Don’t use any of the other keys and come straight back to us when you’re done, okay? Just try and get back before your food arrives.”

Gratefully, Dean accepted the keys, hardly able to believe he was actually being trusted with this. He cast his gaze from Cas to Sam with a murmured, “Thank you,” as Sam shuffled out of the way to let him leave the booth.

Reaching the restroom was awkward, but he made it as quickly as possible and immediately shut himself in a stall. Getting his jeans down to his ankles was the easy part, but he found he was rocking back on forth on his feet in discomfort even while he tried to stay still so he could reach behind him to find the lock. It took him a minute of trying to get the key to slide into it, but he found that if he could hold still for long enough then he was able to feel out the indent of the keyhole and push the key inside. It snapped open and he pulled it away, only to find that he was then faced with the challenge of undoing the strap. Dean gritted his teeth and swore under his breath. He found himself wishing that he’d just asked Cas to come with him, and to hell with the guy he was pretty sure was a few stalls down.

The strap came free, and Dean felt he was just about ready to burst as he realised the butt plug was next. He was going to have to deflate it, but at least he was releasing the enema so he wouldn’t need to inflate it again when it was put back in. It took several agonizing seconds longer, but he managed to work his fingers inside far enough to pry it out. Then, he finally let himself collapse down onto the toilet seat and sighed in relief.

The really hard part, he knew would come when he was finished. Feeling the pressure inside him blissfully ease, Dean took a moment or two to examine the set of keys he was still holding in his hand. He was contemplating just how many of them there were when he realised each one had a number marked on it. At first he thought it would spare him having to count if he just found the highest one, but then he considered what the numbers were for, and glanced down at the tiny padlock at the base of his cock. There was a tiny “6” etched into it. Made sense, he thought. If they had so many keys they’d need an easy way of matching them up to the locks.

When he was done, he gave a groan of frustration as he set about trying to get himself properly secured again. The butt plug was the easy part, it turned out, but getting the strap fastened again was tricky. Dean gave a frustrated sigh and let go of the damn thing as he leaned against the wall of the stall. He should have just asked Cas to come with him. The strap around his waist was feeling loose now too, and honestly everything was just a mess.

While he was standing there, he heard the sound of the restroom door opening again, and then was relieved to hear Cas voice calling out to him. “Dean?”

“Cas?” he answered somewhat hesitantly, but the angel’s next sentence put his mind at ease.

“It’s just me in here, Dean. I checked. You’ve been gone a while. We were wondering if you needed help?”

“Actually, um…yeah,” Dean admitted, defeated. “I’m in here.” He slid back the lock in the stall so that Cas could come in, and Cas raised an eyebrow as his eyes flickered down past Dean’s waist.

“Yes, I think we didn’t anticipate how tricky this would be for you,” he observed as he shuffled into the stall to join Dean and shut the door.

“It’d be easier if I could just see what I was doing,” Dean huffed, and Cas gave him a reassuring look.

“Well, don’t worry about that now. I’ll sort it. Just turn around.”

Dean did as instructed so that Cas could go about getting everything fitted into place again, tightening the straps where needed. Thankfully, no-one walked in on them before Cas had finished and they’d both washed up, before heading back out to join Sam again.

The younger Winchester smiled somewhat apologetically as he saw them approaching. “Everything alright?”

“It is now,” Dean answered, glancing down at the plates of burgers and fries on the table and feeling his mouth start to water.

“The food already arrived,” Sam continued, “I waited for you, but I think it’s gone a bit cold. Sorry.”

“Not a problem,” Cas answered, reaching out with a forefinger to touch the two plates that weren’t salad while Dean was getting himself sat down again. “Should be warm now. Go ahead, Dean. Eat up.”

Dean did, eagerly picking up the burger and biting into it while Sam finally got started on his own food. This was fun, he thought, just being able to spend time with the pair of them doing something as normal as going out for lunch (even if he was wearing a leather harness under his clothes that nobody but the three of them knew about).

They stayed a while even after finishing the food, doing nothing more than talking and enjoying each other’s company for an hour or two. By the time they were about to go Dean had drunk three cups of coffee, and the feeling of fullness was starting to creep up on him again. Sam leaned in closer to his ear again just as they were preparing to leave. “Do you need to piss, Dean?”

Dean nodded.

“You think you can last until we get home?”

Dean considered. “No, probably not.”

“Alright then.” Sam discreetly held up his own set of keys for Dean to take off him. “Same again. I think you can manage the front locks more easily. It’s this one for the plug on the catheter. We’ll be waiting out here for you when you’re done.”

“Okay, thank you.” Dean took the keys off of him gratefully before heading for the restroom again.

Sam and Cas exchanged glances with each other as they watched the door swing shut behind him. “He seemed to enjoy that,” Sam observed with a smile. “We never got him pie, though.”

“Well, I’ll go order some to take out,” Cas said, heading to the counter to make sure Dean had one more thing to look forward to when he got back.


	12. Chapter 12

**Summary for the Chapter:**

> Kinks: basically, getting Dean out of the harness again

Dean ended up eating the pie in the back of the car on the way back to the bunker. It was cherry in shortcrust pastry, one of his favorites, and he thought it was the perfect dessert to end the perfect lunch.

Once they’d arrived back, Cas took the empty pie tray and the fork off him before Sam and Cas proceeded to march him inside straight to the bathroom. They began to undress him until he was stripped down to just the harness again, and then they both cast long, roaming looks over his body. He still looked amazing all bound up like this, but they’d left him like that for long enough.

“Alright, I suppose we best get you out of all this,” Cas said, reaching into his pocket to take out his set of keys. “Come over here, Dean,” Cas instructed, and once Dean had done so Cas grabbed his hips to position him so that he could start unfastening the straps. He managed to get the butt plug and its accompanying strap out before handing Dean over to Sam, who started easing off the nipple clamps and the bindings across Dean’s chest. Dean let out a sigh as the hardened buds throbbed while sensation returned to them, before Sam started working his way down to Dean’s cock.

Sam was about to begin unfastening the straps holding the cage in place when he paused a moment, examining the ring around Dean’s balls. “This has been adjusted,” he remarked, tilting his face up towards Dean’s again. “We had it tighter earlier, didn’t we? Cas, was this how you set it up?”

Dean gulped nervously as Cas leaned down to inspect it. “No, I’m pretty sure I had this tighter,” he said, straightening up to look in Dean’s now burning face. “And I didn’t adjust it earlier, I gave the keys to you.”

Sam rose to his full height now too so that he could stare into his brother’s face. “Dean?”

Dean stared at the floor, feeling very awkward. All he’d done was make it ever so slightly looser where it was connected to the cage, since he’d noticed the lock matched up to one of the keys Sam had given him and he wanted to be more comfortable. “I’m sorry, Sammy,” he apologized quietly, “Sorry, Cas.”

Sam gave him a stern look. “I didn’t tell you you could use any of the other keys, Dean. I just said you could unplug the catheter.”

“I know. I’m sorry. It’s just that it was hurting a bit and I thought you wouldn’t mind if I adjusted it a little.”

Sam let out a heavy, disappointed sigh. “Dean, no. We trusted you to only use those keys for what we gave you them for. You know what you should have done if you wanted it adjusting?”

Dean swallowed, not wanting to look Sam in the eye, but forcing himself to do so. “Ask you to do it?”

“Yes.”

“But I thought I was meant to be going to the bathroom on my own…?”

“Then you know what else you should have done?”

Truthfully, now that he thought about it, Dean knew the answer to that too. “Asked permission before I left?”

“Exactly.”

On the other side of him, Dean heard Cas sigh too. “You understand this is cause for punishment, Dean? You disobeyed.”

Feeling really horrible to have spoilt what had been such a great time, Dean nodded. “Yes, I’m sorry. I didn’t think you’d mind.”

“But that’s just it, Dean. You didn’t ask, just assumed,” Cas reiterated. “Right, we’ll get you out of this, then Sam and I are going to have to do something to punish you.”

Dean just nodded meekly as Sam got back to work taking the cock cage off, which turned out to be far less enjoyable that it would have been. Sam unfastened the locks where the ring attached to the cage, allowing him to slide the tube off Dean’s tightly bound cock. It flopped free as the metal slid away, looking a little pink from being squeezed so tightly. The end of the catheter was still protruding from the tip, but Sam wasn’t ready to take it out before he’d untangled Dean from the straps and slid the cage off fully.

Sam stood up again to look Dean in the face, still seeming displeased. “I’m going to take the catheter out now,” he explained, cupping Dean’s dick with his left hand and pinching the end of the tube with his right. “Just a warning: this will hurt.”

Dean barely had chance to brace himself before Sam had jerked his hand back to pull the catheter out. It was sudden, sliding out quickly but painfully as Dean felt the burn all the way along the inside of his shaft. He cried out, but Sam didn’t react. Once the tube was removed, the younger brother immediately closed a fist around Dean’s soft dick and rubbed it a couple of times so that Dean felt the ache inside his cock more sharply. He whimpered a little before Sam let go.

“Okay,” Sam said gruffly, eyeing Dean up and down and noticing the way he was anxiously biting his lip. “That’s that done. We are going to have to punish you now, Dean. Just because we took you out for a treat and let you have the keys, it didn’t mean you could use them without our permission.”

Dean nodded, knowing Sam was right. The lingering taste of the cherry pie felt bitter in his mouth now as he realised he’d spoiled things, but at least they were going to get the punishment out of the way quickly. It wasn’t like either of them to drag things out.

While Sam had been doing that, Cas had gone to retrieve Dean’s collar. He fixed it back into place and clipped Dean’s leash to it, before handing control of the leash over to Sam. “Hands,” Cas ordered, and Dean obediently brought his hands up in front of him so that Cas was able to use one of the now free straps from the harness to bind his wrists together. Dean could feel blood beginning to rush to his still sore cock as he grew nervously excited for what was to come. He didn’t know how they were going to punish him, but he thought he was ready to find out.

“Alright, now come with us,” Sam growled at him, and then gave a harsh tug on the leash to lead Dean back through the bunker to where he would be disciplined.


	13. Chapter 13

**Summary for the Chapter:**

> Kinks: bondage, punishment, cock whipping, aftercare

They were back in the dungeon. The table from earlier was still there, equipped with restraints, and Cas and Sam dragged Dean over to it and laid him down. He could feel his heart pounding with excitement and nervousness as they secured him into place, pushing his knees apart and then strapping down his ankles, before maneuvering his still bound hands above his head and fastening them to the table.

While Sam disappeared from Dean's view for a few moments, he saw Cas standing over him, devouring his body with his eyes. The sight only made Dean's cock harden faster, throbbing reddened and stiff where it hovered over his stomach. Cas glanced at it, and then returned his gaze to Dean's face, reaching out to gently caress his cheek. The gesture was surprisingly tender, given how stern and displeased he and Sam seemed to be.

Dean leaned his head into the touch, and then Cas' fingers trailed downwards along his jaw and throat to come to rest against Dean's chest. Cas pressed lightly against Dean's heart, feeling the fluttering beat that was shaking his ribs. "Are you nervous, Dean?" the angel asked softly.

Dean swallowed and nodded slightly. He felt very exposed and vulnerable like this, but they had his trust that they wouldn't do anything he didn't want.

Cas gave a nod of acknowledgement, accepting that Dean was anxious about what was about to happen. They wanted to make him nervous, but not to push this to the point where it stopped being enjoyable. Soothingly, Cas rubbed against Dean's chest with the pad of his thumb. "Your heart's beating very hard. Is that because you're excited or afraid? Be honest, Dean."

"A bit of both," Dean answered, sounding a little breathless.

"But would you still like us to punish you?"

This wasn't a test, and Dean knew he was free to answer truthfully. "Yes, please."

"Okay." Cas' hand returned to Dean's face then and gently stroked his forehead. "We need to make sure you learn to behave yourself and ask permission for things, Dean. Sam is going to get your cock cleaned up first before we punish you."

Sam returned at that point, carrying a bowl of water and a cloth, which he set down between Dean's legs. "Alright, it's time to get you freshened up," the younger Winchester said, before he proceeded to start wiping down Dean's cock and balls. Dean let out a gasp, finding the texture of the damp cloth and the water temperature very pleasant. Sam was thorough, making sure to wipe down the inside of Dean's thighs and getting underneath his balls, which he made a point of kneading firmly as he cleaned them. He finished off with some rough scrubbing of Dean's cock, which was approaching the point of painful before he set the cloth to one side. Dean let out a grunt. It wasn't easy for him to keep his head lifted to see what Sam was doing, so mostly he kept it back against the table and his eyes shut as the sensations swept over him.

The next thing Dean felt was Sam gently dabbing his cock dry with a soft towel, before the sharp smell of disinfectant filled his nose and something cold and wet was being rubbed onto his cock with Sam's bare hands. Dean thought that using disinfectant on him was perhaps a little excessive, since the smell wasn't exactly pleasant, although he did enjoy the sensation of having it applied. But it did make him wonder how exactly they planned to punish him.

In the time that Sam had been doing that, Cas had disappeared from sight to prepare something else, but now he returned so that Dean could see both of them standing between his legs. He strained his neck slightly in order to stare down at his cock and see what they were both doing to it. Sam had moved the basin of water out of the way, and now they were both standing grinning at the results of his work. "Much better, Dean," Sam said, "Your cock's looking very pink and clean now, and it's so pretty when you get it hard for us. It almost looks good enough to taste, but unfortunately we can't do that right now. You've given us no choice but to punish it."

They then held up another couple of items for him to see, and Dean felt his heart speed up. Cas was holding a cock ring, fitted with studs on the inside designed to dig into his flesh, while Sam had hold of another ring for his balls and a leather strap. A whine escaped his throat that was a mixture of excitement and trepidation. They both proceeded to fit them onto him at once. Had he not been hard, Sam's ring would have gone round both his cock and balls to stop him hardening at all, but it seemed that they wanted his cock erect. Instead, Sam simply slipped it around his balls and tightened it until it dug in painfully. Dean yelped.

Cas, meanwhile, had pushed the studded ring over Dean's cock and then fitted it just underneath the head, adjusting it so that the blunt studs compressed Dean's flesh uncomfortably without doing any damage. With both rings fitted into place, Dean sucked in a sharp breath of pain, wondering if his punishment was going to be another endurance test, but it seemed they weren't finished.

Cas flashed Sam a grin. "You get his cock stretched out for me. I want it nice and taut," he said before disappearing from view again, and then Sam licked his lips and got back to work on Dean's cock. The leather strap he was holding clipped onto a loop on the ring below Dean's glans and then the other end attached to Dean's collar, which Sam proceeded to fix in place before adjusting the length. Dean cried out again as he felt it pulled tighter so that the studs dug even more painfully into his flesh, although the feeling of his cock being stretched was actually quite enjoyable.

Sam kept going until Dean's cock was pulled back to rest completely flat against his stomach, leaving the sensitive underside completely exposed. Dean's balls were kept held down out of the way by the ring around them, but he knew by now that the discomfort from this was unlikely to be the punishment in itself. He felt a flutter of nerves swirl in his gut.

"Sammy, what are you going to do to me?" Dean asked quietly in a slightly unsteady voice.

"What we have to to teach you your lesson," Sam answered, although not sounding as stern as he could have. He actually gave Dean a smile. "Don't worry, Dean, I'll make sure everything's okay. I know you'll be a good boy and take your punishment: we won't make it too much for you."

He moved then to go and stand by Dean's head, beginning to stroke Dean's hair to try and soothe the anxiety coursing through him. That job only became even harder as Cas reappeared again.

Dean's eyes widened and he felt his heart give a painful kick against his ribs as he saw what Cas was holding. It was a flogger: made of soft suede and with six narrow tails protruding from the handle. The texture would be too soft to cut him, but the slender width of them was sure to make the blows sting like hell. As Dean realized where the blows would be landing, he felt his head begin to spin.

They were going to whip his cock.

The thought gave him a rush of simultaneous excitement and fear. Any sensations on his cock, as long as they were inflicted safely, were usually enough to get him off, and the sheer kinkiness of this was giving him a joyous thrill, but at the same time, _they were going to whip his cock._ Dean didn't balk at pain in the bedroom, but when they were going to do it to an area so sensitive, it was enough to get him more than a little nervous.

He shuddered as he felt Cas bring the thongs to rest against his cock and drag them gently across his flesh. "You've been a bad boy, Dean, and we're going to teach you a lesson. Do we have your consent for this punishment?"

Dean licked his lips and stared up at Cas wide-eyed. Whatever reservations he had, he wanted this. "Yes."

His voice had shook when he answered, and noticing his uncertainty, Cas raised a hand to rest on his cheek. "You seem very nervous, Dean. I need you to be sure. Twenty lashes is what I'm asking you to agree to."

Dean stared steadily back up at him, having made up his mind. "I'm sure. Punish me, Cas. Please."

Cas nodded and then took a step back so he was in the right range to bring the flogger down. The angel gave one final glance at Sam before beginning. "Keep an eye on him. If you think I need to stop before he does, tell me."

Sam nodded his acknowledgement and kept one hand stroking Dean's hair while he kept a close eye on Dean's reactions, making sure they didn't push him too far.

Once satisfied that they were ready, Cas began.

As the first blow landed on the soft, tender flesh of his cock, Dean screamed. He hadn't meant to, wanting to endure his punishment more stoically for them, but the pure shock of it forced the cry from his throat. The tails stung his cock wickedly and he felt the throbbing aftershocks of the lash course through him even after Cas had pulled the flogger away. It hurt like hell, but he still wanted more.

When the second lash came, Dean was more prepared and managed to supress his cries, but by the time of the third he was screaming again. The build up of pain with no time to recover was too much.

Sam stroked his hair gently in the time between the third and fourth lash, and leaned down to press a kiss against Dean's sweat slicked brow. "Shh, it's okay, Dean. Let it all out if you have to. When you're loud it proves what you're willing to endure for us, and we really appreciate that. We know you can be brave for us."

The succeeding blows prompted Dean to cry out again, and his body writhed violently as he pulled at his restraints. It looked phenomenally hot to Cas and Sam, the way his muscles rippled and his exposed skin gleamed with sweat, but only so long as the expression on Dean's face showed there was a rush of pleasure to accompany the pain.

By the time the ninth blow fell, Dean seemed too exhausted to scream loudly anymore, lying still and producing only a faint whimper as the suede flogger struck hard across his cock. By the time of the twelfth, he was almost completely silent save for his heavy, shuddering breaths, and tears were streaming down his cheeks. He hadn't safeworded, but it looked like this had passed the point of enjoyment.

Pausing, Cas exchanged a look with Sam. The younger Winchester had his fingertips pressed into Dean's throat, feeling that his heart rate had rocketed up to the point of strain that showed he was at his limit. Silently, Cas lowered the flogger and then walked over to join Sam, bringing up his hand to gently stroke Dean's face and wipe away the tears. "Dean, would you like to take a break?" he asked softly.

Dean unscrewed his reddened eyes open again to look up at Cas, but his jaw remained tightly clenched as he gave a small nod.

"That's okay, Dean," Cas reassured. "We don't have to do it all right now. Would you still like us to continue?"

Dean managed to croak out a verbal answer for that, proving that he had, up to a point being enjoying it. "Yes...please. It's just very intense. Can I please have a rest?"

"Of course, Dean," Cas said, leaning in to kiss his brow while Sam gently kissed Dean's temple. They only enjoyed inflicting pain on Dean as much as Dean liked receiving it, which oftentimes was a lot, but they knew they were testing his limits.

It took nearly fifteen minutes before Dean's breathing had steadied again and his heartbeat felt to be at a more comfortable pace. "Are you ready for me to continue, Dean?" Cas asked, and Dean's nod of affirmation was quite strong and certain.

"Would you like me to hold your hand this time?" Sam offered, and when Dean nodded again, he took hold of one of Dean's bound hands and squeezed it tightly.

Satisfied they were ready, Cas took a pace back again and proceeded to deliver the rest of the blows. He spaced them a little less frequently this time and paid close attention to Dean's responses. He was screaming again, raw and loud, but with the definite sound of pleasure to every cry and clearly not trying to hide the extent of his pain from them. It was both incredibly satisfying and arousing.

They didn't know if Dean had been deliberately holding off, but when the final blow fell, he came. An exhausted, tired whimper slipped past his lips as he spilled weakly over his chest in several short spurts, and then he fell still. He may have orgasmed, but the experience wasn't exactly pleasant.

Once it was over, Dean was left a trembling, weak-limbed puddle upon the table. Cas immediately put down the flogger and went to unfasten Dean's restraints while Sam continued to soothe him. "There, there, Dean. You did so well, and you were very brave. Now you've taken your punishment we can put that behind us. We're going to take care of you and put you to bed."

Cas cleaned Dean up with the cloth and then undid the strap to allow his now soft cock to hang loose again. As soon as Cas had finished completely untying Dean and removing the rings, Sam scooped up his brother's limp, naked form in his arms and began to carry Dean back towards the bedroom. Cas followed.

Once they arrived, Cas pulled back the sheets on the bed for Sam to lay Dean down into, and Sam settled Dean's trembling body upon the mattress before tucking him in. Cas pressed a quick kiss to Dean's forehead before he had to leave the room to fetch something, and then Sam sat himself down on the bed beside his brother

Dean was shaking, but there was still a slight upturn to the corners of his mouth to show that he was happy. "Are you okay, Dean?" Sam asked gently.

Dean grunted his response hoarsely but earnestly. "Yeah. My cock fucking hurts now, but I'm glad you did that."

Sam smiled a little, relieved that Dean hadn't found it too much. "Do you think you've learned your lesson?"

Dean was almost tempted to say no, as the thought of having them do that to him again was strangely appealing, but he found that the pain deriving from it outweighed the pleasure."Yeah, I know how to behave now for you, Sammy."

"Good boy," Sam said with a smile, before he proceeded to kiss Dean's brow affectionately. Dean returned the grin with one of his own, marred a little by the way his brow was creased in pain.

Hoping to take his mind off the discomfort, Sam got up from the bed and started to strip his own clothing away, making sure Dean got to enjoy the view of him fully naked. The smile on Dean's face told Sam that he liked what he saw, before Sam pulled back the sheets and clambered into bed beside Dean. He reached an arm out to pull his brother tighter against the warmth of his own body before kissing him again, this time on the lips. It was deep and tender and Sam could feel Dean relaxing into him. "You just rest now," Sam whispered, "Cas is going to take care of your cock and make sure it's alright, then you can go to sleep.

Dean shut his eyes and nestled down into the crook of Sam's neck.

Cas returned a minute or two later, carrying a black doctor's kit bag that he'd brought up from the infirmary. He smiled as he saw Dean settled down contentedly in Sam's embrace, but he disturbed him a moment later as he set the bag down on the end of the bed and pushed the sheets up past Dean's crotch.

Dean started and his eyes fluttered open, but it was Sam who pacified him. "Shh, it's okay. Cas just needs to take a look at your cock and make sure it's alright."

Dean relaxed then as he realized what Cas was doing, and spread his legs to allow the angel access. Cas reached up to take hold of Dean's cock and lifted it to examine the underside. It was sore and red with a few swollen welts, but they'd been careful to use a flogger that wouldn't break the skin.

"I'm going to put some antiseptic on this, Dean," Cas explained, "And I brought you some painkillers. Take them with this." He reached into the bag to produce two pills and a water bottle filled with red liquid, which he handed to Sam.

Sam placed the pills on Dean's tongue and then helped him swallow by holding the bottle to his lips. "It's cranberry juice," Sam clarified. "To stop you getting an infection from the catheter."

A grumbling sound from Dean's throat as he swallowed showed his thanks.

Cas began to work on Dean's cock, taking out a tube of antiseptic cream and then coating Dean's length with its contents. It was soothing, and Dean let out a contented sigh as the cool balm eased the burn. Cas was generous with it, thickly coating the stinging red flesh of Dean's cock until it was almost completely smothered. Dean was happy to let him. He knew Cas could heal him if he wished, but he got more attention by letting him do it the traditional way, and even though it hurt, it meant he got to have Cas handle his cock.

When Cas was done with the cream, he took out some bandages from the bag and began to wrap them around Dean's cock. Dean gave a sharp hiss of pain from the pressure, but it was better to have the sore area bandaged than free to chafe and rub on things. Cas bound Dean's dick firmly from the base right up his length, just leaving a gap for the unmarred head to peek through. When finished, he packed the bag away and set it on the floor, before leaning down to affectionately press a kiss to Dean's tip. "That should be fine in a few days, Dean," he said as he pulled the bedsheets back down over Dean's legs. "I expect you're exhausted, but it's okay, you can sleep now. We'll decide what else to do with you in the morning."

Cas stood up and began to undress, letting Dean watch before he clambered into the bed opposite Sam and snuggled up next to Dean. "Goodnight, Dean," he whispered, reaching over to turn out the light on the nightstand and then returned his arm to its position draped over Dean's waist.

Dean closed his eyes, still feeling a stinging pain in his cock, but more than content as he settled down between the pair of them and began to drift off to sleep.


	14. Chapter 14

**Summary for the Chapter:**

> Kinks: not really any this time, tbh. Just fluff.

**Notes for the Chapter:**

> A brief, fluffy, Sastiel-ish interlude, because I wanted to include something like this at some point and this felt like a good time to do it. TorchwoodCardiff, I promise medical kink next chapter!

The room was dark in the early hours of the morning. Dark enough that it would have been almost impossible to see for a human, but of course for Cas it was no problem. The angel wasn’t sleeping, like he never did, but for once he hadn’t closed his eyes and gone through the motions of a nightly human cycle for Sam and Dean’s sake. His eyes were open, and he’d propped himself up on one elbow to stare down at Dean, raising one hand to gently card his fingers through the hunter’s hair. Dean looked so beautiful when he was sleeping. Peaceful. Vulnerable, even, and it made Cas just want to lie here and watch over him for hours.

On this night, he wasn’t the only one doing so. “Sam?” Cas murmured softly. “You awake?”

A soft “Mmm,” from the other side of the bed answered him. “It’s not easy to sleep when he’s right here in front of me.” Sam couldn’t see Dean in the blackness as clearly as Cas could, but the hand he had resting on his brother’s chest was softly and affectionately stroking across Dean’s skin and feeling out the shapes of his body. Cas could make out the gentle smile on Sam’s features. “Gorgeous, isn’t he?” Sam whispered softly, seeming entranced by the figure sleeping soundly between them.

“So much,” Cas whispered back, although in truth he thought it was an understatement.

“You know, I love this,” Sam continued contentedly. “That we can make him happy this way. Sharing him beats fighting over him.”

Cas returned Sam’s smile warmly. “I like doing this with you as well, Sam. We work well together.”

“We do. It’s fun planning things; figuring out what he’d like.”

They both stared down at Dean for a few moments, contemplating that, and then looked back at each other. Tenderly, Cas raised the hand he was using to stroke Dean’s face and reached out to tuck a strand of hair behind Sam's ear. The pad of his thumb brushed Sam’s cheek as he did so, and he allowed it to linger there for a few seconds.

Sam watched him steadily, focusing as well as he could in the dark, and then by unspoken agreement they simultaneously leaned over Dean’s sleeping body and pressed their lips together. The kiss was soft and lingering, their lips gently but firmly touching for a few seconds. It was so unlike the times they’d done this before. Their previous kisses had been infrequent, usually much rougher and fuelled by frustration, serving to make Dean immensely jealous of both of them. Which, of course, was half the reason they’d done it. But now, the kiss was a genuine expression of love. Working together to please Dean had definitely drawn them closer.

After a few moments, their lips gently drew apart although their faces remained hovering close together, eyes locked on each other’s. “That was pleasant,” Cas commented warmly, and Sam smiled.

“It was. We should do this more often.”

“Do you think Dean would like that?”

“I think he’d be turned on by it.”

“Then you’re right; we should do this more often.”

They kissed again, a little more forcefully this time as they parted their lips and gently pushed their tongues against each other. It didn’t last long, just a brief confirmation of affection between them before they pulled apart again and returned their attention to Dean. The elder Winchester was sleeping soundly between them, oblivious to what was going on above him.

“You should get some sleep, Sam,” Cas said, settling himself down more snuggly in the bed beside Dean. “You’ll have less fun with him tomorrow if you’re tired.”

“I know,” Sam replied as he burrowed himself further down in the sheets, bringing his head to rest against Dean’s shoulder. “I just need to make sure he’s alright. I think we really strained him today.”

“He’ll be fine, Sam,” Cas reassured. “We’ll take good care of him. You get to change his bandages tomorrow, and you know he’ll love that.”

Sam grinned sleepily, eyes closed as he settled against Dean’s skin. “I know. So will I.”

“Good. You should rest then. I’ll watch over you. Both of you.”

“Thank you, Cas,” Sam murmured, listening to the soft rhythm of Dean’s breathing gently lulling him to sleep. It didn’t take long for Sam to join his brother in unconsciousness, and soon Cas felt them both breathing deeply and evenly in time with each other. The angel smiled, pressing his face into Dean’s soft hair as he reached his arm out further to drape over both of them, feeling an intense, loving protectiveness towards the brothers as he closed his eyes and waited for the morning to come.


	15. Chapter 15

**Summary for the Chapter:**

> Kinks: giving a blow job with a sore throat

**Notes for the Chapter:**

> TorchwoodCardiff, I know I promised medical kink this chapter and it was meant to be coming, but this first part went on a long time so I've decided to split the intended chapter in two. I'm sorry for making you wait even longer, but I'm sure you can see where this is going.

Morning dawned on cue in the bunker. The artificial lights flickered on to coincide with the rising light levels outside, since the place had no windows. It was about 8:30 when Dean woke up, although Sam had regained consciousness about a half hour previously. He'd chosen to remain in bed so as not to wake Dean, but now that Dean had woken on his own, Sam smiled at him warmly. "Good morning," the younger Winchester affectionately greeted his brother.

Bleary eyed, Dean stared back at him, wanting to return the smile, but he found that doing so wasn't easy. The feeling that he'd woken to was an unpleasant one, full of a woolly head and aching limbs, as well a throat that felt like sandpaper. All he managed to do was grunt.

Sam immediately noticed something was wrong. "Are you feeling okay, Dean?"

"I don't know. I guess…" Dean replied hoarsely, trying to downplay it, but on his other side he saw Cas leaning over him, looking concerned.

The angel pressed an insistent hand against Dean's forehead and frowned. The skin below his touch was burning hot and clammy. "You're feeling very feverish, Dean. This has come on very suddenly. You must have caught something when we took you to the diner." He and Sam exchanged glances, both silently re-evaluating what they were going to do with Dean now. They hadn't been expecting Dean to get sick.

"I'll be fine, Cas," Dean croaked out. "It's just a cold. You can still have fun with me…" He honestly felt like crap, but he was still pleading with them not to tone down their activities on account of him being ill. The only thing he could imagine worse than feeling like this was feeling like this and being denied their attention because of it.

"What you should be having right now, Dean, is bed rest," Cas said firmly, pressing a hand to Dean's shoulder to keep him down while he himself got out of bed. "Sam and I will take care of you. I'll go fetch you some medicine."

He pulled on a bathrobe and left the room, and Dean moaned uncomfortably as Sam tried to fluff the pillows to give him something to lean back against. They both eventually ended up sitting back against the headboard with Sam's arm wrapped around Dean, who had collapsed against Sam's shoulder.

"I'm sorry, Dean," Sam muttered into his brother's slightly sweat dampened hair. "We didn't mean for you to get sick. Maybe we should give you some vitamins to boost your immune system."

"'S okay, Sammy," Dean mumbled back groggily. "I'm sorry for the trouble."

"Don't say that, Dean. We want to take care of you. It's always our pleasure."

Cas returned shortly carrying a tray upon which he'd set two mugs. "That's to help with the cold," he said, nodding at the mug on the left. "And that's to take the taste away afterwards."

Sam took the left mug off of him, shuffling himself slightly before he raised the mug to Dean lips. "Here, drink this," he said, soothingly stroking the back of Dean's head, and Dean obediently sipped at it.

A scowl flashed across his features at the bitter taste, and Dean wished they could have just given him pills instead of whatever formula this was. Cas had clearly tried to sweeten it with honey, but the sharp acidity of the medicine still bit through to leave an acrid taste lingering on his tongue. It took a long time for him to drink it all, and a disgusted grimace remained on his face afterwards.

Sam looked at him sympathetically, knowing they'd given Dean the worst flavored medicine even if it was most effective. "It's okay, Dean, we've got you some hot chocolate to make it taste better," he said, offering him the second mug. Dean accepted gratefully.

The second drink was finished more steadily than the first, and after Dean was done Cas took the mug off of him and returned it to the tray. "What you need now, Dean, is some rest without us disturbing you," the angel said. "Sam and I will get up, but you stay in bed and try to get some more sleep."

Dean was tired and he did actually want to go back to sleep again, but the rather clingy part of him didn't want them to leave him alone to it, and he felt lousy enough that he didn't mind complaining. "No, please stay. It'll make me feel better."

Sam was getting up now and pulling on a bathrobe. "You're contagious, Dean. Do you really want to give me a cold too?"

Dean scowled, but saw his point. If Cas wasn't going to cure him with his angel mojo, then Dean thought maybe he should just play along and see what they decided to do. "Okay," he mumbled, sinking back down under the covers again. "I'll go back to sleep."

"We'll come and check on you later, Dean," Cas said as they were about to leave the room, "And if you aren't feeling any better, we might have to take you to a doctor."

There was a suggestive inflection in his voice, and as Dean understood what he meant, the corners of his mouth twitched in anticipation. That was something he could be patient for. "Thank you, Cas," he said, closing his eyes again. "Will the doctor look at my cock too? It's still really sore."

"Of course, Dean," Sam promised. "Now you just get some rest."

Dean had settled himself comfortably back down and looked very sleepy again, and with both of them satisfied he would do as he was told, Cas and Sam left him to it.

When they came back a couple hours later, Dean was fast asleep again. They both watched him silently for a few moments, taking in the beauty of his sleeping form, although it was made somewhat less peaceful by the way his lips were parted awkwardly and his breathing was coming uncomfortably heavy. It was with a slight sense of regret that they had to wake him, although they knew he’d feel better in the long run if they did.

In the time that they’d left him on his own, both Cas and Sam had gotten properly dressed. Now Cas was carrying a tray laden with orange juice and a bowl of soup into the room, so Sam went to perch himself on the bed beside Dean and gently shake him awake. Dean was groggy and disoriented as he slowly came round, as well as a little shaky from the fever, and Sam rubbed his back soothingly as he helped him sit up. “Here, Dean, we’ve brought you some chicken soup. That should help.”

The smell of it seemed rather off to Dean as he inhaled as much as he was able through his stuffy nose, but he was grateful for it all the same. Once he was sitting upright, Cas sat down on the opposite side of the bed to Sam and rested the tray in Dean’s lap. Sam then picked up the spoon to start feeding his brother the hot liquid, who tried his best to lean forward and make things easier. Dean was readily compliant as he swallowed down each offered spoonful, although there was a grimace on his face that showed he was finding it painful to swallow. Cas allowed him to take a drink of the cool, soothing juice after every few mouthfuls, hoping that the vitamin C would aid his recovery. Dean looked grateful for the food, although by the end he was still a little shivery and clearly in pain.

As Sam began to shift the empty bowl and cup away, Cas tenderly stroked Dean’s hair, wanting to comfort him. “How are you feeling Dean? Is your throat really sore?”

Dean gave a small nod, his neck muscles seeming stiff. “Please, I think I need something creamy to soothe it,” he said in a hoarse voice, staring at Cas eagerly, and Castiel couldn’t help but smile a little at the ingenuity of Dean’s request. Even when he was bed ridden with a virus, that clearly didn’t kill his appetite for sex.

“What were you thinking of, Dean?” Cas asked coyly.

“I’d like some come, please. I think it would make my throat feel better.”

Cas actually smiled a little then. Dean knew how to milk the situation, when normally they wouldn’t have allowed him to make requests. “Alright, Dean,” Cas said, deciding that if Dean wanted it, they’d do what he requested. “Since you’re sick, I’ll let you choose this once and you can decide which of us you suck off. Me or Sam?”

Dean blushed, feeling a little bad about his answer when it was Cas asking, but Sam’s cock was a little bigger and he did have a tendency to produce more semen. Dean genuinely did want to taste it. “I’d like Sammy’s, please,” he answered shyly.

Sam had gotten up to put the tray on top of a cabinet across the room, but he seemed a little entertained by Dean’s request too. “Aren’t you worried that my cock might strain your throat, Dean?” he said as he turned back round. “It’s already kind of a tight fit for your mouth and you’re not breathing too well at the moment.”

Although Sam wanted to give his brother the pleasure he requested, he genuinely had concerns that it wasn’t a good idea. Not so much for his own sake, as he knew Cas wouldn’t let _him_ stay sick for long, but because he doubted how pleasant the experience could truly be for Dean.

Dean, however, had already out-thought his argument. “But Sammy, you went to the diner too and you didn’t get sick, so your immune system must be stronger than mine. If you let me have some of your come it might help me get better. So isn’t it worth it?”

That managed to draw amused smirks from both Sam and Cas. Of course, the argument didn’t hold up under any kind of realistic logic, but for the sake of their play, Dean was spinning quite a good case. His determination to get what he wanted was definitely winning them over. “Okay, Dean. If you really feel up to it, you can suck me,” Sam conceded, beginning to unzip his jeans. “How shall we do this? Are you alright to get out of bed?”

“Here, let’s try this,” Cas suggested, taking a throw blanket from the foot of the bed and wrapping it round Dean’s bare shoulders as he helped him out of the sheets. The angel then took a couple of pillows and placed them on the floor beside the bed for Dean to rest on. “If you kneel on these, it might be comfier for you,” Cas said as he helped Dean ease his sore limbs down onto them, all the while trying to keep the blanket wrapped tightly about him to alleviate his shivering. “And if Sam sits on the edge of the bed, would that be a good height for you?”

“Yes, thank you,” Dean said quietly. He still sounded ill, although his tongue swiped eagerly over his lips as he watched Sam pull his pants and underwear down to his ankles. The younger Winchester sat down on the edge of the bed in front of his brother and spread his knees, offering his cock up at head height to Dean. He wasn’t hard yet, and Dean stared down with a keen gaze to watch his erection grow. Of the three of them, Sam’s cock was definitely the largest, matching the size of him in general, and Dean loved to see it standing up stiff and engorged. “Would you like to finger me or touch my cock?” he offered to help Sam harden faster.

“No, Dean, your cock needs time to recover and you aren’t well,” Sam declined, starting to rub his own cock to encourage his hard on, although Dean’s sheer eagerness was definitely helping. “This won’t take long.” Cas was kneeling beside Dean to help keep the blanket around him and maintain his comfort, although the look on his face showed he was impressed by Dean’s enthusiasm. With Dean staring hungrily at Sam’s crotch, it didn’t take long for Sam to get fully hard. “Here,” Sam offered, grasping his stiffened member at the base and then pointing it in the direction of Dean’s mouth. “Now you can have a suck.”

Slowly, Dean leaned forward and opened his mouth wide to close around Sam’s tip. The younger Winchester reached up to gently cup the sides of Dean’s head and guide his movements. Normally, Sam was quite rough when it came to receiving blowjobs and he domineeringly preferred face-fucking to passive receiving, but with Dean in this state there was no way Sam would force him to deepthroat. He kept his hips still and allowed Dean to control the depth and duration of his sucks so that he was able to breathe. Dean’s tongue was enthusiastic, lapping fiercely over Sam’s shaft, but his sucks were quite shallow and he couldn’t draw Sam in any more than a few inches. As pleasant as it was, and despite the couple of particularly nice moments when Dean tongued at his slit, it still wasn’t enough to bring Sam much closer to orgasm.

Sam felt a slight twinge of guilt as he noticed how hard Dean was working, yet the younger Winchester still couldn’t manage to get himself to finish. He wanted to give Dean the thick, soothing creaminess he’d asked for, but Dean’s mouth wasn’t quite doing enough to get him there and Sam didn’t think his brother was currently capable of doing much more. Dean himself was clearly getting frustrated, and a short while later his mouth popped off of Sam’s dick as he stared at the floor in embarrassment. “I’m so sorry, Sammy. I can’t get you off,” he mumbled in a voice that sounded even more raw and pained. “I promise I’m trying. I don’t mean to be bad.”

Cas was giving him a concerned look as he continued to rub Dean’s back, and Sam tried to reassure him. “It’s okay, Dean. You’re sick. We can’t expect you to be at your best,” he said as he reached up to gently stroke the side of Dean’s face. “I can tell you’re trying very hard and your mouth certainly still feels very nice. Don’t worry, I can still finish for you.”

“You just need a little help, Dean,” Cas offered, and then he raised himself up off the floor and spat on his own fingers before reaching behind Sam to seek out his hole. He located the opening just above where Sam was perching right at the edge of the bed, and then pushed a digit inside. A sharp burst of air was pulled into Sam’s lungs in a quick gasp, and a grin spread over his face as he felt Cas’ finger ease further inside. This was such a rarity for the pair of them to do this to each other, and the novelty of it only turned him on even more. He hoped Dean was enjoying getting to watch.

To find out, Sam’s eyes flickered back down to Dean’s face, who was clearly staring enthralled at the sight before him. Evidently, he loved it and felt very jealous at the same time, if the protrusion of his semi-hard cock beneath the blanket was anything to go by. The bandages and the soreness would be enough to prevent him getting a full hard on for a while, but if he’d gotten it up that far, then he must really be aroused. “You keep sucking me, Dean,” Sam gasped out a little breathlessly. “Cas will help me come.”

Obediently, Dean immediately returned his mouth to Sam’s cock, trying his best to pleasure his brother while Cas provided assistance. The angel’s fingers were working quickly, briefly exiting Sam’s body to have more spit applied before returning and working further inside. Cas rubbed in firm, deep strokes along Sam’s walls, complementing the wet heat of Dean’s mouth, and Sam soon found himself becoming lost in the sensations. A few well-timed jabs against his prostate had him grunting in ecstasy, and then he jerked his hips forward and spilled himself into Dean’s mouth.

The stars in his vision cleared quickly as his final hard spurt declined to one last trickle, and almost immediately he regretted how rough his movement had been. He hoped he hadn’t hurt Dean, but his brother, it seemed, had loved every moment of it. Dean was eagerly licking up every drop of come that he could reach with his tongue, exploring further down Sam’s length although he was still struggling to take in his brother’s now softening member much further. The initial bursts of hot semen had gone straight to the back of his throat, and he was thankful for it. The warmth had immediately soothed the sorest areas without him having to strain his throat muscles to swallow, and the viscosity of it was still clinging on and easing the dry scratchiness.

A dazed look had settled on Sam’s face as the force of his orgasm left him reeling, but both he and Cas were staring contentedly down at Dean who appeared to be feeling much happier for having gotten to taste Sam’s come. After a minute or two, he let Sam’s limp member flop from his mouth and stared back up at them with a smile to accompany his still bleary eyes. “Thank you for helping, Cas,” he croaked out. “Thank you, Sammy. I’m really grateful for you letting me swallow your come.”

“That’s alright, Dean,” Sam said, tucking himself away again and zipping his jeans up as Cas went to help Dean back up onto the bed. “Let us just take a look at your throat now and see if it’s helped.”

Cas had Dean sat back on the side of the bed by now, and the angel’s hands were probing gently at his neck. “Open wide, Dean,” Cas ordered, and Dean did so to allow Cas to stare into the back of his mouth.

A frown settled on the angel’s features as he carefully studied the reddened tissues of Dean’s throat. “I don’t think it’s helped much. This still looks inflamed,” Cas declared. “You need to see a doctor, Dean. We’ll take you to one and he can give you a full check-up.” A hand on Dean’s jaw prompted him to close his mouth again as Castiel leaned away, exchanging a glance with Sam. Sam suppressed a grin, knowing what they had planned.

“Come here, Dean,” Sam said, reaching out to pull his brother’s feverish, blanket-engulfed body closer to him. “Now, why don’t you wait here with me while Cas makes us an appointment to see the doctor, then I can take you down to get examined in a short while.”

Dean curled up closer against his brother, his body shivering but lips curving upwards in a grin. No matter how lousy he was otherwise feeling, he wanted them both to keep playing with him.

Sam and Cas exchanged one final look as the angel prepared to go get a new play session set up for them in the infirmary. They knew this was one of Dean’s favorites. “Okay Dean, let me go arrange things for us,” Cas said before he went to go get things prepared, leaving a rather feverish but excited Dean shaking giddily in Sam’s arms.


	16. Chapter 16

**Summary for the Chapter:**

> Kinks: roleplay, medical kink. Lots of it.

**Notes for the Chapter:**

> TorchwoodCardiff, I finally got round to it! And this is still only about half of what I originally had planned. I don't know if you were perhaps hoping for something more realistic, but fantasy med fet sceneplay is more my thing, and there's probably still a couple more chapters of it to come. So...yeah. This is the part at which I apologise to readers who don't care for medical kink as much as the other stuff in the story. You can skip to chapter 18 if this isn't your thing.

About half an hour later, Sam decided it was time to take Dean for his doctor's appointment. "Come on, Dean, let's go get you examined," he said, wrapping the blanket more tightly around his brother's body. Dean feebly clutched onto the soft fabric for comfort, and Sam frowned a little at how sick and exhausted Dean looked. He hoped their activities wouldn't prove too demanding for him, even though he seemed to be enjoying them, but Cas could always cure him fully if it ever reached the point of being too much. "The doctor will help make you better," Sam reassured as he reached under Dean's back and knees to pick him up bridal style. "I'll carry you there if you're too tired to walk." It was a good thing he was strong enough, although he suspected Dean was completely capable of walking if he wanted. But Dean allowing them to coddle him like this certainly was't something he minded. 

Dean curled up close against Sam's body as he was carried down to the infirmary, acting more weak and feeble than he actually felt. True, he had a cold and it sucked, but it wasn't totally unbearable. It was just more enjoyable for him to play along with their attempts to baby him.

When they got there, it transpired that Cas had set out a chair in front of the closed infirmary door, and Sam sat Dean down onto it before going inside. "I'm just going to see if the doctor is ready for you. Wait here," he instructed as he opened the door and then closed it behind him, leaving Dean in the hallway with his arousal and excitement increasing by the minute.

It took another five minutes or so before Sam returned again, this time with a mischievous smile spread across his face. "Doctor Novak will see you now," he said, waiting at the door, and Dean got stiffly to his feet and walked over to join him.

Upon entering the infirmary, Dean saw Cas had arranged everything the 1950s facility was equipped with to look as much like a functional modern clinic as possible. Apparatus and equipment were laid out ready for use, and Dean glanced over at the examination table to see that a couple of pillows were resting on it and it still had the stirrups attached. They were folded away under the table, but still deliberately on display for him to see.

Cas himself was there and waiting for them. He'd donned a white coat over a smart suit accompanied by a stethoscope draped around his neck, shedding the role of Dean's personal angel Dom to instead act as his doctor. The sight alone was enough to get Dean's heart beating a little harder.

"Mr. Winchester," Castiel said, casting only a brief glance at Dean as he addressed Sam. "How can I help you today?"

"It's my brother, Dean," Sam explained, gently nudging Dean's back so that he took a step further forward. "He's sick and he needs you to take a look at him."

Cas turned his attention fully onto Dean then, eyeing him up and down hungrily. Dean felt the full force of his stare as Cas' eyes raked over him, almost as if they could penetrate through the feeble covering Dean wore. Castiel's face showed arousal, but his voice hid it when he spoke in a tone that was cold and clinical. "Very well, if you could get him to remove the blanket so I can examine him."

He spoke to Sam, not Dean. The younger Winchester repeated it for his brother's benefit, phrasing it more softly. "The doctor needs to have a look at your body, Dean. You'll have to take the blanket off."

In truth, the only reason Dean wanted to keep the blanket on was because he was actually shivering, despite the heat burning just below his skin. He was having the horribly contradictory experience that came with bad colds of burning up while simultaneously feeling chills, but he thought he could tolerate it. He slackened his grip on the blanket so that Sam was able to slip it off his form and expose his body to Cas.

Just the slight twitch of Cas' mouth betrayed his enjoyment. The angel's eyes flickered downwards to Dean's bandaged and semi-stiff cock. "Has he obtained a recent injury to his penis?' Castiel asked in the same tone as before.

"He misbehaved," Sam explained for him. Cas of course knew what the bandages were for, but Dr Novak didn't. "And unfortunately had to be punished."

The 'doctor' nodded, and then proceeded to pick up a clipboard from the nearby desk and apparently make a note of that. "In that case, would you also like me to perform a genital exam?"

Sam nodded. "It's been a while since we've taken him to a urologist. I'd appreciate it if you can inspect all his parts."

Castiel nodded again. "I'll also perform a genital exam and a rectal exam on him, then, if he's due a check up in that area. Could you clarify the nature of his illness?" Cas was noting Sam's responses down as he went along.

"Fever, stiff limbs, tiredness, sore throat, difficulty breathing," Sam listed, and the doctor jotted all that down on his clipboard before setting it down to one side.

"Thank you, Mr Winchester," he said to Sam, and then returned his attention back to Dean. "Right then, Dean. I understand you're feeling a little sick, so I'm going to perform a full physical on you, if you'd like to come over to the exam table." He indicated with a wave of his hand where Dean should go, and Dean obediently followed. "Just sit down on the side of it, for now. I'll begin with the basics."

Dean had to admit, Cas had got the doctor's style down well. Not that he would tell either of them, but he thought that Cas played the role even better than Sam, although that was probably because Cas had actually caved when Dean tried to persuade him to watch a marathon of _Dr Sexy._ If Dr Sexy was the inspiration for this, Dean found it even more of a turn on.

Dean did as he was told, looking forward to what was coming next. He saw that Sam, meanwhile, had taken a seat by the desk to give himself a good view of the proceedings, and was currently grinning as he waited for the exam to commence.

Cas started simple, bringing up his fingers to feel at the glands in Dean's neck and then shone a penlight into his eyes and ears. It wasn't the part of the examination Dean enjoyed most, but he knew they were most likely saving the best parts until last. Touching him like this was just enough of a tease if he could be patient enough to wait.

"Open wide, Dean," Dr Novak ordered, and Dean obediently stretched out his jaws for Cas to examine his throat. Instead of the wooden stick on his tongue Dean had been expecting, Cas thrust the index finger of his left hand into Dean's mouth and used that to press his tongue down. Dean blinked once or twice in surprise, but he certainly had no complaints.

The doctor shone the penlight to the back of Dean's mouth, carefully inspecting what he could see. "Say, 'ahh'," Cas instructed, and Dean tried his best to get his strained vocal chords to work. Cas watched the movement at the back of his throat. Dean's tonsils seemed very swollen and reddened, and there was still a thick film of whitish mucus coating the opening of Dean's oesophagus. "Has he swallowed some semen recently?" Dr Novak asked of Sam.

"Yes," Sam replied. "He's something of a cockwhore, doctor, and needs to taste it frequently. He had some of my come less than an hour ago."

Castiel nodded, fingers still inside Dean's mouth.

"Good. I'd prescribe some more of that. Some healthy semen and a good sized cock to massage his throat should be soothing."

Dean made the "ahh" noise again, although this time it was more of a salacious whine.

"He had some trouble sucking me earlier," Sam said, "Is that something I should be concerned about?"

Cas continued to study Dean's throat carefully for a moment and then leaned back, leaving his finger in Dean's mouth. "Suck," he ordered, and Dean obediently clamped his mouth down around the digit. There was an unusual but pleasant taste on Cas' skin, as if the angel had deliberately smeared his hands with something nice for Dean's benefit, and Dean lapped at it eagerly.

The doctor's brow furrowed as he made his assessment. "His sucks are a little weak, but that's to be expected. Take good care of him and he should be able to take your cock again in no time."

Well this was the filthiest doctor's exam he'd ever had, Dean found himself thinking. And he liked it.

Castiel roughly pulled his fingers out and gave Dean a hard stare. "Lay down flat on the table, Dean. I'm going to examine the rest of your body."

Dean did as instructed and swung his legs up to lay down flat on the examination bed, resting his head against the pillows. The next part of the check-up was pure teasing as Cas proceeded to touch every part of his body _except_ for his cock. The angel's touch was warm and sensuously un-clinical as it swept over Dean's skin. Dean felt Cas run his hands up his legs and between his thighs; press down on his abdomen and chest; tap and rub at his nipples; feel inside his armpits; probe his neck...all the while leaving his cock and balls alone. Considering that his cock was still sore, Dean wanted their attention on it soon, but there was still something very pleasant about the way Cas firmly massaged the rest of his body.

"The rest of him seems fine," the doctor declared, straightening up and turning to Sam. "I can feel no abnormalities or glandular swelling. Your brother has an exceptional body, Mr Winchester, and if you want to keep playing with it you have to keep it in good shape."

Sam nodded his acknowledgement. "I know, doctor. That's why brought him to you."

"You did the right thing. He is a little run down. I can show you some procedures to take care of him at home, if you like? I'm going to take his temperature now, which is something you could learn to do yourself, if you'd care to help me."

Sam stood up then, wearing a grin at the prospect of getting to help examine Dean. "What do you need me to do, Doc?"

“First, you can fetch me the thermometer,” Cas said, gesturing to a table where a tray of instruments was spread out. “It’s the blue one with the digital display on the handle. There’s some rubbing alcohol and petroleum jelly there, if you wouldn’t mind cleaning and lubing it.”

He’d been given the more menial preparation task, but Sam didn’t mind as long as he got to watch whatever happened next. He went to do as instructed while Castiel turned his attention back to Dean. “Now, Dean, I need you to turn over onto your front,” he ordered, and with a grin tugging at the corners of his mouth, Dean obeyed. They were finally getting to the fun part.

Cas licked his lips as the soft curves of Dean’s ass were exposed and offered up to him, looking plump and delicious. There were still faint scratches on his skin from their session with the strap a couple of days ago, but it appeared to no longer be hurting, unlike Dean’s cock. Cas wanted to make sure that it wasn’t sore from where it was pressed down against the table. “Are you feeling comfortable?” Cas asked once Dean was in place.

“Yes, Dr Novak,” he answered politely. He was still aching and somewhat uncomfortable all over his body, but the examination was proving to be a very effective distraction and he wanted them to keep going. Out of the corner of his eye, Dean could see that Sam had returned to stand beside the table again, and his own breathing quickened.

That didn’t go unnoticed by Castiel, who grinned as he saw Dean’s excitement. He turned to Sam. “Would you like to insert it?”

“Yes, I think I would, doctor,” Sam answered, looking thrilled that he’d been asked.

Due to the angle of his neck, Dean couldn’t see what was going on behind him, but that only made things more thrilling as he wondered when and where they were going to touch him. Castiel bent down closer to his ear to explain things in more detail. “Your brother is going to insert the thermometer into your rectum via your anus, Dean. I’ll make sure he’s careful so that there’s no tearing of your rectal wall, but this is the best way for us to take your temperature. I’m going to spread your cheeks apart now to make things easier for him.”

The next thing Dean knew was warm, calloused hands were cupping his ass cheeks and pulling them apart, before a narrow, slick probe started to slide inside him. He gasped and wriggled, and Cas pushed down harder to keep him still.

“If you keep moving, Dean, you’ll tear your rectum,” Cas warned, and Dean tried his best to stop squirming from the pleasure that was coursing through his body.

“How far should I go, Doc?” Sam asked Cas, and the doctor glanced down to see how much of the thermometer was still visible protruding from Dean’s ass.

“A couple more inches,” he answered, and a low whine sounded in Dean’s throat as he felt the rest of the probe slide into him. They left it in place for a few seconds before the temperature readout on the display settled down to a constant value. “100.4 degrees,” Castiel read out, giving a nod to Sam to indicate he could slide the probe out of Dean’s ass again. “He’s a little feverish. I can prescribe him some medication for that, Mr Winchester, but I’d also recommend you give him a cold shower after you take him home.”

A cold shower seemed very appealing to Dean right now, who could feel the sweat clinging to his skin as he continued to burn up. However, if there was something even better coming next, he could wait. The thermometer had been fun enough, but he was looking forward to having something bigger up there. Hopefully, it would be a set of fingers. Either Sam’s or Cas’, he didn’t mind, but he hardly dared hope for both.

After pulling it back out of Dean, Sam handed the thermometer back to Cas, who placed it down on a tray to be cleaned. “Since we’ve got him partly opened up already, I think we should do the rectal exam now,” Dr Novak continued, moving over to another tray and taking out two pairs of disposable latex gloves from a box. He tossed one of them to Sam. “This is something else I can show you how to do, Mr Winchester, and you’ll want to occasionally check him to make sure there’s no damage to his anus and that his prostate is functioning properly. You did a good job with the thermometer, but now we should check there was no accidental damage to his rectum.”

Sam pulled on the offered gloves, feeling a thrilling flutter in his own stomach at the thought of what he was about to do to Dean.

“I’ll get him to change position,” Cas said, crossing to Dean again. “Dean, I need you to roll over onto your left side and bring your knees up to your chest.”

Although his joints still ached, Dean managed to do as he was told. He’d just gotten himself in position when he felt Cas’ hands – now rubbery and latex coated – spreading his ass cheeks again.

Castiel took a moment or two to visually inspect Dean’s anus. The sight of the clenching pink pucker was something he enjoyed very much, and he found himself remembering how incredible it felt when Dean’s sphincter would tighten and spasm around his cock, but he managed to hide his thoughts and maintain the semi-professional role he was playing. “There’s no anal fissure. He looks healthy on the outside,” Dr Novak declared as he straightened up and reached for the pot of petroleum jelly to begin lubing up his fingers. Sam followed his example. “We can begin the internal exam. You can penetrate him first, Mr Winchester, but I’ll help guide you.”

Feeling incredibly aroused, Sam stepped up to the table and positioned his fingertips at Dean’s entrance. A shudder ran through Dean’s body. “What am I looking for, Doc?” Sam asked.

“Any bumps, lesions, tears…things that feel out of the ordinary,” Cas answered. “Just one finger for now should be enough.”

Dean took a deep breath as he prepared himself for what was about to come, and then he felt Sam’s finger push insistently inside him. The breath he’d been holding quickly left his lungs in a short burst.

Sam gave his finger a wriggle, rubbing firmly around Dean’s walls and feeling out the textures and contours inside his body. Despite his best efforts to keep quiet, Dean let out a hoarse whine.

“Everything feels good so far,” Sam informed the doctor. “Shall I check his prostate?”

Cas flashed him a grin. “I’ll help with that,” he said, coming to stand beside Sam. Dean barely had chance to brace himself before he felt a second finger sliding past his rim. Now both Sam and Cas were feeling around inside him, and Dean didn’t know how this could possibly feel any more amazing.

He found out a moment later as Cas flicked at his prostate, and couldn’t help but let out a garbled yell. Castiel ignored him. “You feel that?” he said instead to Sam. “That little bump there? That’s his prostate.”

Sam of course knew what Dean’s prostate felt like already, but he was playing along. He wriggled his finger around a little more until he located it. “Ah yes, that one there?”

Dean was falling to pieces, his cock pulsing and still only painfully semi-hard, but they both continued as if they hadn’t noticed. “Yes, that feels healthy,” Cas said. “It’s a normal size; just a bit broader than your fingertip. That’s what you should be feeling for at home.”

Sam gave Dean’s prostate another delightful poke as they both continued to rub at it. The sensation made Dean’s head swim and he thought he was just about ready to come. He could feel his balls were swelling and precome was beading at his tip. Bandaged or not, his cock damn well wanted to be hard. He whined again.

This time, Cas chuckled at the sound. “I think we need to be careful. Too much pressure on the gland will strain him.”

Dean _wanted_ to be strained. Hell, they could rub that little sweet spot all day and make him come over and over until it hurt and he’d still be happy, but Cas and Sam had other ideas. Much to Dean’s dismay, their fingers pulled out of him again. A quiet, disappointed whimper slipped from his mouth as he heard the snap of latex behind him while they disposed of their gloves. He was sick and feverish and sore and all he wanted was just for them to give him a mindblowing orgasm to make him feel better, but when they’d had chance, they’d chosen not to.

It almost made him want to pout and sulk and, for once, to act a little bratty when they didn’t get him off, but then he realized this wasn’t over. Behind him, he heard Cas speaking again, this time with a purposeful licentiousness to his voice. “Now that we’ve established he’s healthy in that respect, shall we proceed with the rest of the exam…?”


	17. Chapter 17

**Summary for the Chapter:**

> Kinks: medical kink, heartbeat kink. Basically my #1 and #2 favorite kinks, so you'll have to excuse the self-indulgence this chapter.

Cas was jotting stuff down on his clipboard again, making note of Dean's temperature and any other observations. As he set it back down on the desk, Sam saw that he'd scrawled the word 'slut' next to his record of Dean's reaction during the prostate exam. Sam smirked.

"What's the next part of the physical?" he asked Cas.

"Well," the doctor began. "He seemed to get a little worked up just now when we touched his prostate. I'd like to perform a cardiovascular exam as a way to assess his stamina."

Dean was still lying with his back to them, but they both knew he was listening. "Yes, I'm sorry about that, doctor," Sam apologised loudly so that Dean could hear. "He does tend to get excited easily, since he _is_ a slut."

They could see Dean's toes curl and his hips wriggle as Sam relayed what Cas had written in his notes. He fucking loved this.

"In that case, I'd like to make sure his body is able to cope with the strain, if he gets so easily aroused," Cas said as he approached the bed, pulling a trolley of apparatus with him. "Okay, Dean, I need you to sit up for me again. Just on the edge of the bed, if you please."

Dean eased himself slowly upwards, wondering what was coming next. As he turned round, he saw that Cas had rolled over a tray of instruments with him and was now picking up a blood pressure meter.

"I'm going to take your blood pressure now," Dr Novak said, and Dean bit back his growl of frustration for them to just make him come already. This next part of the exam was, of course, all teasing again. They'd pushed him to a point just shy of orgasm and were now deliberately refusing to do anything else to take him beyond it. He'd just have to be patient.

 _A patient patient. That's a lame joke,_ Dean thought, even as it occurred to him.

Wanting them to get on with things, Dean offered his arm out for Cas to slip the cuff in place. It tightened uncomfortably while the doctor took his blood pressure, which Cas jotted down before sliding it off him again. "That's in normal range," Cas announced as he pushed the equipment to one side. "Right, Dean. The next thing I need to do is examine your heart."

Dean swallowed painfully, already feeling a little embarrassed by just how fast his heart was beating. It was an even clearer giveaway of the extent of his arousal and frustration, but he didn't mind letting Cas feel it.

"I'll start by palpating your chest," the doctor said and took a step closer to Dean. His previously cold voice had assumed a tone that was much more seductive as his eyes lowered from Dean's face to scan down his torso. Dean's lips parted as he watched him approach, his breathing coming quick and shallow while a flush of heat bloomed under his skin. He felt Cas' hand settle on the left side of his chest.

Their eyes met for a moment while Cas glanced upwards, and Dean felt his sense of embarrassment increase further. The doctor began to slide his fingers down Dean's pectoral muscle and curve them around his ribs, before a thumb swiped over his left nipple. Dean gasped.

"Was that painful?" Cas asked softly, noticing his reaction.

Dean quickly shook his head. "No..."

"Good," the doctor responded, returning his thumb to the nipple again and gently compressing it. His fingertips dug into the skin just below the peak before they started to rub his areola, and Dean started to wonder if Cas was actually trying to feel for his heart or just enjoyed playing with him.

"Mr Winchester, I need your assistance," Castiel said, and promptly Sam stepped up to stand beside him. So far, he'd just been enjoying the show. The frustrated look on Dean's face was priceless.

"What is it, Doc?"

"His heartbeat should be most palpable on his chest in this region here," Cas said, stroking the area around his nipple again. "I need you to compress it while I check his carotid pulse."

With a grin, Sam waited for Cas to remove his fingers and then replaced them with his own, pressing down firmly on the little protrusion of pink skin. It was pliant beneath his fingertips, and Sam dug his nails in just slightly to make Dean squirm. He found that if he pressed down hard enough, he could actually feel the flutter of Dean's heart beneath his nipple.

Cas, meanwhile, had shifted himself to bring his lips close to Dean's neck. He intended to feel with his mouth rather than his fingers, and after a brief moment his lips descended to press against Dean's pulse point. Dean tensed and his breath hitched. Cas' mouth opened and he began to suck hard to make the blood beat even harder against the surface, and Dean held his breath as the hot pressure of Cas' mouth pressed down.

The suction was in satisfying contrast to the sharp pressure Sam was exerting on his chest. Fingers were pushing down hard against his nipple, rolling and squeezing it so that he felt a sharp pinch of pain, but he wholly welcomed it. Dean's eyes flickered upwards to meet Sam's gaze, who was staring at him intently, and he blushed even harder. His cock was throbbing again.

Cas continued to suck hard at his throat for over a minute before he pulled back, leaving behind a tingle on Dean's skin. Immediately, his 'professional' role was resumed. "His pulse feels healthy. A little fast, but his circulation is strong. Thank you for your assistance, Mr Winchester."

Sam pulled his fingers away sharply so that Dean's nipple gave a throb. "Of course, doctor," he said, taking a step to one side.

Castiel made another note on his clipboard and then put it back down. "Right then..." Dr Novak resumed, taking the stethoscope from around his neck and fitting in the eartips. "I'm going to listen to your heart and lungs now, Dean. This may be a little cold at first, but it will warm up. Lean forward for me."

With his heartbeat already coming a little faster, Dean did as he was told, and then he felt the cool metal press against his chest as Castiel started to listen. The doctor made no comment, but moved the stethoscope around Dean's chest as he paid close attention to the sounds coming from inside. At one point he pressed the bell up close to Dean's left nipple, again flicking at the already overstimulated bud with his fingertip, which triggered a little jump in Dean's heartbeat. Cas grinned.

"Take a deep breath and hold it for me, Dean," he ordered, and heard the rhythm of Dean's heart change just slightly as Dean obeyed. It sounded beautiful. "Okay, you can let it out again now," Cas said after a few seconds, and Dean exhaled steadily before the doctor removed the stethoscope from his chest and instead pressed it onto his back. He continued to move it around for a short while longer as he listened intently.

After a couple minutes, Cas took the chestpiece away and pulled the earpieces out again. "His heart sounds healthy," he told Sam. "It's thumping very hard, but his breathing is a little raspy. With the right medicine that should clear up in the next few days. Now," - he turned back to Dean again - "Dean, I need to do a stress test on your heart to make sure it still sounds good and strong when you're a little more strained. That will require some genital stimulation, which I'll ask your brother here to apply. I'm also going to let him listen to your heartbeat so he knows what a healthy rhythm sounds like for you. It won't be anything too taxing for you, Dean, but I need to measure the elevation in your heart rate when you have your penis touched."

Dean nodded his understanding, growing increasingly excited.

"Right," Castiel said, now addressing Sam. "Mr Winchester, you'll want to be between his legs for this part. There's some stirrups underneath the table if you could fold them up into place, and then go fetch that stool over and take a seat. I'll get him moved down the bed."

Cas helped Dean shift his position while Sam got things set up, and soon Dean found himself lying flat on his back with his ankles in the air while Sam stared intently at the space between his legs. His cock, while not fully hard, wasn't hanging limp, and it had stiffened a little to jut out slightly above his ball sac. Sam was smiling at it, but Dean felt the discomfort of the bandages tight around his swollen member. "Doctor," he said in a small voice, feeling shy about addressing Dr Novak directly. "My cock is hurting. Will that affect your tests?"

"It will be fine, Dean. I'll see to it that your penis gets treatment," the doctor replied unaffectedly. "Mr Winchester," he then said to Sam. "I'm going to ask you to remove the bandages, since we can't properly stimulate his penis with them on. However, since the tissues are slightly damaged, I need you to perform a full genital exam on him before we proceed with the stimulation. I'll explain to you how to do it, since this is something you should perform on him at home quite frequently."

"Thank you, doctor. That would be helpful," Sam replied with a grin. "Shall I take the dressings off now?"

"If you would. Allow me to inspect the damage before we proceed any further."

At last, Dean felt a thrilling tingle run through his cock accompanied by a sharp sting as Sam began to unwrap the bandages from his chafed flesh. Soon, he felt the coolness of the air caressing his cock as blood quickly rushed into it now that there was more room to fill, and he bit down hard on his bottom lip. His reddened skin throbbed painfully as his erection swelled, but it was more than worth it.

Castiel had gone to hover behind Sam's shoulder as they both watched Dean harden. "I see what you mean about him being a slut," the doctor remarked in amusement. "That didn't take him long. His injuries seem sore, but not too severe. We can deal with them afterwards. For now, I need to monitor his heart while you examine him." He then moved back to the right of Dean and repositioned the stethoscope to rest against his heart. The rhythm was much faster with excitement, which Cas found incredibly pleasing. Dean's heart was a less obvious part of his body than his erect cock, but it betrayed his arousal just as much.

"You'll want to start with his testes," Cas instructed Sam. "Feel them for any kind of lumps or abnormalities. They should feel soft and compressible, so check if they're swollen of have any visible lesions, and test if they feel the same on both sides."

A gasp slipped from Dean's mouth as Sam immediately set to work, fondling and squeezing his balls as he gently cupped them. His fingertips pressed into Dean's tender flesh and he rolled both balls in his palm, testing their weight. Dean's pulse jumped, and Cas chuckled.

"Careful, Mr Winchester. If he's as much of a whore as you say, he'll be very sensitive down there. You don't want to strain his heart."

"Is he already getting excited?" Sam asked with a lick of his lips.

"Yes," answered Cas, who was now gripping onto Dean's wrist to take his pulse. "His heart rate is elevated to 106 beats per minute. When you've finished the exam, I'll let you listen."

Sam used both hands to gently tug on Dean's balls and stretch them downwards, and then let them dangle freely between his legs again. "His testicles feel healthy. I couldn't detect anything out of of the ordinary."

"Just to be sure, try feeling with your tongue," Cas suggested. "The mouth can be more sensitive at detecting abnormalities than the fingers."

Just hearing that sentence was enough make Dean's pulse race faster before Sam was even able to act on it. At the moment he felt his brother's warm mouth close around his balls, Dean whimpered and trembled. His cock throbbed hard and all his other discomfort was momentarily forgotten as he became aware of nothing but Sam's hot tongue lapping and pressing into the small mounds between his legs.

Sam made sure to do a thorough job and licked over every inch of Dean's sac that he could reach before pulling his mouth back. A huge grin had settled on his features. "Everything feels normal."

Cas seemed satisfied. "Good. His heart is beating very fast, but still sounds healthy. Come and take a listen."

Sam got up and went to accept the stethoscope Castiel was offering. He pressed the end down hard against Dean's chest, and his grin widened as he heard how wild he'd made Dean's heart go. "That sounds very strong," Sam commented on the thundering rhythm.

"It is," Cas replied as he took the stethoscope back off him. "He has a lot of stamina. Now you need to take a look at his penis."

Still smiling, Sam went to reposition himself back between Dean's legs and awaited Cas' instruction.

"You'll need to be careful because of his injuries, but if you could try feeling along his length for any lumps."

Sam did as instructed, moving his fingers tenderly, and Dean sighed and shut his eyes in pleasure. He felt Sam pull his cock downwards before tugging it in various directions to examine it thoroughly, and it felt amazing. "All clear," Sam declared when finished.

"That's good. The next part you'll need to check is his foreskin." Cas reached into his pocket then and held out a penlight to Sam, who took it. "Roll it back and look for any inflammation or discoloration of the skin underneath."

As Sam pulled at the senstive skin on his tip, Dean grunted and jerked his hips. That earned him a stern reprimand from the doctor. "Stay still, Dean," Cas snapped, and Dean tried his best not to move.

The penlight was shone underneath the thin skin peeled back from Dean's cockhead, illuminating the beads of precome that were dribbling steadily from his tip. "It looks pink and healthy under there," Sam relayed to the doctor.

"Check inside his meatus as well," Cas instructed, and Dean was about to say "My what?" when he suddenly felt Sam's tongue swipe over his tip, cleaning away the clear fluid that was obstructing his view. That hadn't been an explicit part of Cas' instructions and was clearly improvisation on Sam's part, prompting Dean's heart to stutter.

"He tastes healthy," Sam said with a grin, and then pinched Dean's tip with his fingers as he shone the penlight into Dean's slightly widened slit. Sam studied it carefully for a few moments before declaring, "Everything looks clear down there."

Dr Novak nodded in satisfaction. "That's all good, Sam. His heart rate is still around 130, which is where it should be. You've almost finished the exam now, you just need to apply the stimulation to his penis. It will be less effective if he's in pain, so I recommend applying some cream to his injuries first. We can bandage him up afterwards."

He offered Sam a tube of antiseptic which Sam proceeded to apply generously to Dean's cock.

"I need him to ejaculate," Cas elaborated while Sam worked. "If you can try to get him to deposit a sample in here, and I'll monitor his heart rate while he orgasms." Cas had given Sam a small plastic cup for Sam to jack Dean off into, and he positioned it in place as he prepared to stroke Dean's cock.

Dean felt an immense wave of relief wash over him as he realised that, at last, this was the part where they were going to let him come. It was, however, tainted with apprehension at the thought that they were going to rub his injured cock to do it.

Cas shifted himself around the bed so that he had a good angle from which to view things while at the same time keeping the stethoscope pressed over Dean's heart. Once in place, he gave Sam a nod to show that he could start. "You may begin. Take it steady at first and build up to finishing him. We don't want to cause him further injury."

Sam nodded his acknowledgement and then carefully reached out his fist to wrap around Dean's length. His initial touch was infuriatingly loose and feather-light, and Dean gave a frustrated whine before Sam tightened his grip. Then, slowly, he began to pump.

As Dean felt the firm pressure working its way up and down his length, he felt grateful for the thick cream coating his cock. The strokes were tight but slippery so as not to be too rough on his sore skin, and it felt good. Sam's hands still stung, but it was a pleasant, welcome kind of pain that helped the tingling pressure between his legs build faster.

As Sam quickened his pace, Dean cried out, yelling with the sharp twinges that shot through his cock. His heart kicked into his ribs right below where Cas was pressing the metal head of the stethoscope against him, and he thought it must sound to Cas like he was going into cardiac arrest right now. Sam's strokes were becoming frantic, feeling much rougher as most of the cream had already rubbed away, and Dean was screaming hoarsely in a combination of ecstasy and agony.

Almost mercifully, it was over quickly. With a couple more forceful, quick tugs, a final yell tore from Dean's throat and he erupted into the cup Sam was holding out for him. He came in one long spurt this time, taking several seconds to empty his balls before collapsing down with an exhausted whimper.

Sam set the cup to one side and then moved to stand beside Dean, gently stroking down his arm. "It's okay Dean. It's all over now," he soothed, although he thought that the sight of Dean on the examination table yelling as he painfully came was the hottest thing he'd seen in a while. He turned to Cas. "How was that, doctor?"

Castiel, too, was grinning. Watching Sam jerk Dean off had been fun for him too. "His pulse was very erratic towards the end, although his heart seems strong enough to cope. His reproductive organs also seem to be functioning very well, judging by the volume of his deposit." That was said with a smirk. "What I'm going to prescribe, Mr Winchester, is some cold meds and a lot of bed rest. I'll also give him a booster shot to get his vitamin levels up." He crossed then to the trolley of instruments to pick up a syringe that had already been filled, and tested it by squirting a small amount of clear fluid from the end. "Could you please keep him still while I give him this?"

Dean looked too exhausted to put up much of a fight anyway, but Sam went to hold his hand and make sure he didn't move while Cas pushed the needle into his arm and depressed the plunger. The only sound Dean made was a faint exhale of breath.

"All done," Cas said as he pulled the needle out and swabbed the area down with a cotton bud. "You can take him home now, Mr Winchester. Make sure you give him a shower to bring his temperature down before you redress his penis. Also, he'll need to keep taking these." He offered a small bottle of pills to Sam, who slipped them into his pocket before going to wrap Dean up in his blanket again.

"Thank you, doctor," he said once he had Dean's trembling and utterly spent form scooped up back in his arms. "You've been a great help."

"It was my pleasure," Castiel replied, wearing a huge grin that showed he truly meant it. "If you ever have any more problems, please don't hesitate to bring him back to me."

Sam carried Dean back out into the hallway, smiling down at the tired but contented expression on his brother's features. "You were so good for the doctor, weren't you, Dean?" he praised, and delighted in the way Dean's lips twitched upwards in response. Warmly, Sam dipped his head to press an affectionate kiss to Dean's brow. "Now, you heard what he said. Shall we go find Cas to give you that shower? And then I can bandage your cock again and you can go back to bed."

That all sounded very appealing to Dean. "Yes please, Sammy," he mumbled into Sam's shoulder, feeling happiness sweep over him despite all the physical pain he felt. If this was the kind of treatment they gave him when he was sick, then he thought he wouldn't mind getting ill more often.


	18. Chapter 18

**Summary for the Chapter:**

> Kinks: shower sex, voyeurism

The next place Sam took Dean was the kitchen to get him a glass of water to help swallow the pills. He placed two capsules on Dean's tongue and then raised the glass to his lips, and Dean grimaced as he forced his throat muscles to work to swallow them down. It did look painful for him, and Sam felt a rush of sympathy. It was no wonder Dean had been struggling so much to suck him. Clearly, Dean's sexual appetite was currently overreaching his body's limits.

Cas came to join them shortly, having changed back into regular clothes. When he saw Dean sat at the kitchen table still wrapped in his blanket, he immediately crossed over to him and planted a soft kiss on his forehead.

"How are you feeling, Dean?" he asked tenderly, his fingers caressing Dean's cheek.

Dean grunted. "Honestly? Like crap."

"Have you been to the doctor?"

"Yeah."

Sam took over at that point, sparing Dean having to talk much more. "I've given him his pills. Dr Novak says we need to give him a cold shower to bring his temperature down."

Cas looked back at Dean. "Would you like me to do that with you?" he asked as he felt Dean's forehead again. "You're still feverish."

Dean nodded. "Yes, please."

"Okay then, let's get you to the showers."

Dean assured them he could walk this time, so they led him to the bathroom and started up the shower while Cas stripped himself naked. The temperature was cool, not cold, but Dean still shivered as he stepped under the stream of water. It was pleasantly soothing against the heat coursing through his body, but he wondered how long it would be before he'd had enough of the chill and wanted some warmth back again.

The temperature couldn't have been pleasant for Cas, but he joined Dean under the shower head anyway. Dean felt a rush of gratitude for it as the angel started to soothingly rub soap onto his body and cleansed away the sweat clinging to his skin. Sam was stood nearby, watching with a soft, fluffy towel gripped in his hands and ready to wrap around Dean the instant he stepped out of the shower.

"Are you feeling any better, Dean?" Cas asked as he shampooed Dean's hair.

Dean gave him a small smile. "A little."

"When you saw the doctor, did he let you come?"

The question was a little sudden, but Dean glanced over at his brother and smiled a little more. "Sammy did it for me. The doctor told him to rub my cock."

Cas looked pleased as he started to rinse the suds away. "Orgasms are a great medicine, Dean. Would you like another one while we can get you cleaned up?"

Now Dean was definitely grinning. "Yes please."

"Alright then. Come here." Cas wrapped an arm around Dean and pulled him closer against his own body as he reached his now soap-free hand down to cup Dean's ass cheek. He gently squeezed it before extending a finger to slip into Dean's crack and find his hole. There was still lube left inside from the prostate exam and Cas' finger was dripping wet, so entry wasn't too difficult. The angel pushed the digit inside and started to rub, taking great care to apply pressure where Dean liked it most.

Dean groaned and pushed himself harder against Cas' body, his own cock rapidly hardening. He soon found it banging against Cas' own erection as they rutted beneath the streaming water, and his grunts of pleasure became mixed with pain as the impacts stung his cock. Cas pulled his hips back by just a couple of inches as he curved his wrist more to reach further inside Dean, adding another finger. Dean whimpered and turned his head to bury it in the crook of Cas' neck, trying to stifle his cries.

All the while, Sam watched, enthralled. Dean always looked stunning to him, but the sight of him dripping wet and naked was probably Sam's favorite view of anything in the world. The water drenched his hair and plastered it to his skull; before running further down his body in delicate streams that perfectly emphasised every line and angle of muscle tone that Sam loved so much. It was made even better by the euphoric expression on Dean's face that continued to grow in intensity as Cas pushed him closer to the edge, and Sam savored it.

He could almost have focused on nothing but Dean and it would still have been incredibly pleasing to watch, but then there was Cas. It wasn't often that Sam would take a step back and watch the angel in action with Dean, but really, when he paid attention, he found Castiel just as beautiful. His naked body and the look of intense, passionate concentration on his face were further fuelling the sensation of Sam's own pants growing tighter. Sam unzipped them and then slipped a hand inside to palm his cock as he continued to watch.

Cas inserted yet another finger and a ripple of joy coursed through Dean's body. He was biting down on Cas' shoulder now, so close to the edge, and Cas was determined to satisfy him thoroughly. The angel had found Dean's prostate - so cruelly teased barely an hour ago - and this time his was sure to properly attend to it as his fingers flicked and rubbed at the gland.

Dean shuddered and jerked his hips, his cock slamming into Cas' abdomen despite the angel's attempts to avoid aggravating the sore area, and after a further few moments he grunted and came. His spurts were less forceful than earlier, but his cock still gave a few jerks as come spilled from his tip and rinsed away under the water. The intensity of it all left Dean panting slightly and leaning against Cas, shivering now that he’d had enough of the cold water.

Cas held him tightly against the warmth of his own body while he turned the temperature up a little, taking a moment to ensure Dean was properly rinsed down. Sam, meanwhile, had gone to rinse his own hands after having jerked himself off to watching the pair of them, finding the sight just too much to stare at passively. Once he was ready with the towel again, Cas shut off the water and helped Dean step out of the shower and into Sam’s arms. The moment that the soft fabric wrapped around him Dean clutched at it, as if he could tangibly grasp onto the comforting warmth that it provided.

“Let me do it, Dean,” Sam said firmly, not quite stern enough to be a reprimand, but making sure Dean knew to keep his hands off. Realising his mistake, Dean immediately let go and allowed his brother to pat him dry, feeling the towel’s softness against his skin. Sam came to drying down his cock soon enough, gently dabbing at it just briefly before pulling the towel away and replacing it with a fresh blanket draped around Dean’s shoulders to keep him warm. “I’ll get that bandaged for you in the bedroom, Dean, if you’re okay to wait?” Sam said, and Dean nodded. He was beginning to feel a little drowsy from the cold meds, and he was more than happy to go back to bed after this.

Cas had been drying himself off, and he pulled the towel away from himself briefly before going to wrap it round his waist. As Dean watched him, he noticed he still had a hard on. “Cas?” he began to say, his voice hoarse but eager. “Would you like me to suck you?” He’d already sucked Sam today, and he thought it only fair that he suck both of them off since they’d both now made him come.

Cas, clearly, was a little surprised by his request, but politely turned it down. “It’s okay, Dean. I’ll finish myself. You were struggling with Sam earlier; I don’t want to strain you.”

“But Cas…” Dean was struggling to croak it out now, but he really wanted this. “You haven’t got to come yet today, and besides, the doctor said I need some cock to soothe my throat.”

At that, Cas raised an eyebrow and Dean heard Sam chuckle. “You’re insatiable, aren’t you?” his brother said. “And a little demanding. I’m not sure I like this attitude.”

His tone had been light-hearted, but cautionary, and Dean immediately looked apologetic. “I’m sorry, Sammy,” Dean said, glancing at the floor. “I just want to please you both and show that I’m grateful for you looking after me. I don’t mean to be demanding.”

Sam exchanged a glance with Cas, as if asking for his opinion, but Cas seemed prepared to be lenient on account of Dean being sick. “It’s alright, Dean, we’ll take you back to the bedroom and you can suck me, on the condition that after that you go back to bed, and don’t get up again until Sam and I say you’re allowed.”

Dean showed his submission with a bow of his head. “Yes, Cas. Thank you.”

Satisfied with that arrangement, Cas pulled on a bathrobe and they led Dean – still naked save for his blanket – back to the bedroom. This time, Cas laid himself down on the bed and pulled apart the robe so that his dick was exposed, protruding upwards from between his legs and curving back towards his belly. “Alright, Dean. If you want my cock, this is how you can have it.”

Dean bit his lip and glanced at Sam, who made a waving gesture with his hand as if to say, “You wanted this. Do it yourself.” Steadily, Dean crawled up onto the bed and positioned himself so that his head was just above Cas’ crotch. He was probably going to get less assistance this time, so he had to try to make this as good as possible. He swallowed once to test the pain – finding it just slightly duller than earlier – and then stretched his mouth open and lowered it onto Cas’ dick.

Thankfully, Cas was slightly smaller than Sam, although still not by much. Dean tried to bob his head, feeling a tight stiffness in his neck, and pain twinged in the back of his mouth as he managed to suppress his gag reflex. He knew he couldn’t take Cas in any further, but he hoped it would be enough as he started to suck.

Beside him, he felt a compression in the mattress as Sam came to kneel next to him and began to stroke his hair, showing some encouragement. For all his efforts, even after a few minutes it seemed Dean wasn’t able to get Cas off. Taking pity – or maybe just wanting to tease him – Sam crawled further up the bed again to bring his face close to Cas’ and do something to help Dean out.

“Cas…” Sam murmured, reaching down to cup the angel’s cheek and tenderly swipe his thumb along it. Cas stared steadily back up, wondering what he was planning to do as he sensed Dean’s gaze flicker up to them from between his legs. If this was what he thought, then he was very keen to see what would happen.

Just a brief moment later, Sam leaned down and pressed his lips against Cas’, pulling him into a kiss that was all tongues and passion. With his mouth still wrapped tightly around Cas’s cock, Dean stared. A sharp stab of jealousy shot through his gut that for once they were focusing entirely on each other, almost to the point of forgetting about him, but at the same time, he loved how incredibly hot it was. And more than that, he couldn’t help but notice how happy the pair of them looked. They were enjoying this. Genuinely.

That was enough to please him as he recalled how frustrated the constant friction between them had used to make him, and it gave him enough reinvigoration to suck harder to the point where, finally, he felt Cas’ thighs clench around him as the angel spilled his seed down Dean’s throat. Cas and Sam had done so much to reward him, and now Dean had been able to do something to reward them.

By the time Dean had finished swallowing Cas’ come and pulled his mouth away, Sam and Cas had parted again. He looked up to see them both smiling down at him contently. Cas, in particular, had a rather joyous fucked-out grin on his face. The sight made Dean immensely happy.

“Well done, Dean,” Sam praised, since Cas appeared to still be reeling. “You did so well. I think Cas liked it very much. Has that helped your throat feel better?”

“Mmm,” Dean replied, thinking that he was actually feeling a little better than earlier, although that was definitely the last swallowing he wanted to do for the day.

“Alright,” Sam said. “Come lay down then and I’ll bandage your cock, then you can get some more sleep.”

Dean did as he was told and clambered into the bed next to Cas, before Sam got up and hitched up the sheets to his hips so that he was able to dress Dean’s cock again. Dean sighed and turned his head into Cas’ shoulder as he felt his cock once again being smothered in cream and then firmly wrapped up, delighting in the sensations. The underside was still sore, but he could tell it was healing, and Sam was very tender with it. Once he’d pulled the bedsheets back down Sam went to lie next to Dean on top of the sheets.

“Are you feeling comfortable?” he asked gently.

Dean nodded. “Yes, thank you.”

On his other side, he heard Cas speak again. “You know, it isn’t mine and Sam’s bedtime yet, and we aren’t sick. We ought to be getting up again soon.”

It occurred to Dean that if they did get up they might engage in some more fun stuff without him, but he found that, actually, he’d be okay with that if it helped them work so well together. He didn’t, however, much want to be left on his own. He would have tried to protest and beg them to stay a little longer, but Cas’ tone showed he’d didn’t have much inclination to move anytime soon. “Are you going to?” he asked instead.

“Not sure I want to,” Cas replied. “It’s very pleasant lying here next to you.”

Sam chuckled. “Well, I think we can stay for a little while longer, in that case. At least until you fall asleep.”

A warm smile spread across Dean’s face. “Thank you,” he murmured, closing his eyes and sinking further down into the bed. His head was growing woolly again, and the ache in his limbs was still present, but the medication had kicked in and he was both feeling better and rather sleepy. With unconsciousness creeping up on him, his last thought was just how great it was to see them both so happy around each other, before he finally sank back into sleep.


	19. Chapter 19

**Summary for the Chapter:**

> Kinks: penis plugs, cock cages, dildos, cross dressing, maid's outfits, nude photos

Dean was bed ridden for three more days before he felt back to normal again. Cas and Sam had spent that time constantly taking care of him, cuddling with him, making him hot chocolate and giving him medicine even when he insisted he was feeling better, and Dean was grateful for them drawing it out as long as possible. They hadn’t let him leave the bed except to go to the bathroom, and he thought he was going to miss having them attend to him 24/7, but on the other hand, he was looking forward to getting to play properly again.

The bandages on his cock had come off after the first couple of days, after which they’d both said they’d allow him a break, but he knew that today the cage would be going back on, and he was looking forward to it. It was the first thing they did after they gave him his morning shower and brought him through to the kitchen for breakfast, since this was the first time in a while he hadn’t needed breakfast in bed. “How are you feeling, Dean?” Cas asked as he distributed a handful of blueberries onto a waffle to feed to Dean.

Dean smiled broadly. “A lot better, thanks, Cas,” he answered, “You’ve both taken good care of me.”

Sam was smiling too as he set down the mugs of coffee on the table for the three of them. “You know we need to get your cock bound again today, right?” he said, “Don’t want you getting hard all the time and making yourself frustrated.”

Dean nodded. Weirdly, although just a few days ago he couldn’t have imagined having his cock permanently bound, he knew what Sam meant. Whenever they had his cock locked up to control his erections, it always made things doubly rewarding when they freed it again. When he couldn’t get himself off, he only appreciated them doing it for him all the more. “Would you like to put it on now?” he offered, turning in his seat and spreading his legs open so that his cock hung down for Sam to see.

The younger Winchester licked his lips. “I think that’s a good idea, Dean. Cas, have you got his cage today?”

The angel nodded. “I’ll go get it. Don’t start eating without me,” he said before he left the room.

Sam took a seat at the table and continued to stare down between Dean’s legs, absently sipping his coffee as he appreciated the sight. “It’s a pretty thing,” he commented with a smirk. “I’ll miss getting to see it so often.” He then chuckled. “In fact, I think I’ll take a picture of it.” Dean felt heat rising in his face as Sam stood back up and went to the kitchen counter, where his and Dean’s phones were left charging, and picked up his own. “I think I’ll send this to Cas,” he said as he lowered the phone between Dean’s knees and snapped the photo. “He’ll sure like having this to look at. In fact, I think I should start taking more photos of you, Dean. Something to remember all the fun we have by.”

Dean could feel his cock beginning to harden at the suggestion, and he willed it down. He needed to be soft for when Cas came back with the cage. “I’d like that, Sammy.”

Sam smirked. “Of course you would, you slut. You love showing off that sinful body of yours.”

That wasn’t helping much with dissuading Dean’s budding erection, but at that point Cas returned. The angel glanced down at Dean’s crotch as he walked round the table. “Can I not leave you alone for five minutes without you starting to get hard?” he said with a shake of his head. “Come on, I think we need to get this on you before that goes any further.” He knelt down between Dean’s legs to slip on the cage and snap shut the ring round his balls, and Dean felt the heavy, comforting weight tug down on his cock. Cas grinned. “Now, Dean, after your little accident the other day, Sam and I decided we need to keep you plugged up more securely, so we’re going to add this too.” He then held up something for Dean to see, and Dean felt his breathing quicken as he realised it was a penis plug. “I’m just going to push this into your slit,” Cas explained gently, setting the end of the plug at the opening of the cage. “It won’t go down all the way, but it should be enough to keep the tip of your cock stuffed up.”

Dean gasped as he felt Cas slide it inside, loving the stimulation even though his cock was unable to get hard. “Thanks, Cas. Feels good,” he grunted, biting his lip as he adjusted to the sensation. “Are you going to put my butt plug back in too?” he asked once he’d grown more accustomed to it.

“We’ve been thinking about that,” Sam answered as he and Cas took seats either side of Dean, ready to feed him. “It’s been some time since we last put something big up your ass, so we think you need stretching out some more before we can fuck you again. We were thinking a dildo should stuff you up nicely today.”

Dean’s heart skipped a beat. _Yes,_ he found himself thinking. After three days of having not so much as a finger up there, _fuck yes._ “Yes please, Sammy. I need stretching out good for you both.”

 _He’s so eager and obedient,_ Sam thought to himself with a smile, affectionately patting Dean’s thigh. “Of course, Dean. Now you just eat your breakfast first, then we’ll put it in.”

After they were done feeding him, they bent him over the table while Sam slid a broad-based dildo into his ass, leaving nothing but a small jut of plastic protruding from his hole. “Hold on a moment, Dean,” Sam said as he picked up his phone again. “Could you hold your cheeks apart for me?” Dean did so as Sam took a picture, and then the younger Winchester slapped his brother’s thigh to let him know he could straighten up. “Looking great, Dean. How does it feel?”

“So fucking full,” Dean grunted back, thinking he was going to struggle to walk straight today with that thing constantly rubbing over his walls, but damn it felt good.

“Alright, well, we’ve got a special task for you today,” Cas said, casting an appraising glance over Dean’s naked body. “We’ve been so busy taking care of you these past few days that there’s lots of chores we haven’t done. The bunker needs a good clean, so we wanted you to do it for us as a thank you.”

A week ago, Dean would have pouted at the suggestion, thinking it was no fun, but today he was eager to serve them. “Of course I will. You’ve been so good looking after me.” He was wondering how the hell he was supposed to do it when he had a giant plastic dick in his ass that would torment him with every move he made, but he’d figure out a way.

Sam gave a pleased nod. “Good. And like a proper little maid, we’d like you to wear this.” At that point, he walked to one of the cupboards below the sink to take something out of it. He held up what looked to Dean like a small square of white cloth, and Dean frowned at it in puzzlement for a moment until Sam let it unfold to reveal what it actually was. It was a tiny, skimpy apron, complete with pink and white lace frills around the edges, and looked barely long enough to cover Dean’s crotch should he put it on. His ass, of course, would be completely exposed in any case.

Dean felt his face flush bright red as he realised what they wanted. Sam noticed the way his lips had parted in shock, and chuckled. “Come on, Dean. Let’s see you try it on.”

Feeling embarrassed but totally turned on, Dean let them slip it over his head and tie the strings about his waist, before Sam raised his phone again to take another picture. “Suits you, Dean,” Sam commented with a smirk, and Dean felt his cock straining in its cage as he blushed even harder.

“Alright then,” Cas said, handing Dean a feather duster to complete the look. “Let’s see you get to work. And don’t forget what we said about not being shy: if you’re in the same room as us, we want that pert little ass of yours nicely on display.”

Dean swallowed and nodded, feeling his face burn as they both devoured him with their eyes, and then Sam cleared his throat. “You know, I think I’m going to go read in the lounge for a bit,” he announced. “Maybe you want to join me, Cas?”

The angel shrugged. “I think I could do that,” he said nonchalantly, and then both of them turned and left the room.

Dean took the hint. He decided to wait a minute or two before going to join them, a grin spreading across his features as he considered just how he was going to put on a show.


	20. Chapter 20

**Summary for the Chapter:**

> Kinks: feathers, tickling, dildos, orgasm denial

**Notes for the Chapter:**

> I never imagined I was going to get to twenty chapters on this fic, so huge thanks to everybody who's read, commented on and supported this! I think the end's in sight now. I'm not going to estimate how many chapters are left, because I always seem to get it wrong, but I'm planned up to the end now. However, after that keep an eye on the series, because I'll definitely be writing more for this verse.

Much to Dean’s frustration, when he entered the lounge they were actually reading. Sam had his nose buried in _Game of Thrones_ or something or other, and Cas seemed to be concentrating hard on whatever the hell he’d picked up. From what Dean could make out of the cover, it wasn’t even in English.

He got to work straight away, trying not to get distracted by the way the dildo moved inside him and occasionally brushed against his prostate. He had to clench his pelvic muscles to keep it inside him and stop it slipping out, but doing so only made the sensations more overwhelming. At first he tried to keep quiet, but eventually gave in and allowed himself to make soft whimpers every time the plastic cock pressed against that sweet spot inside him. He hoped that would get Sam or Cas’ attention, but if either of them did look up at any point, it was when Dean had his head turned away.

It wasn’t until he got round to doing the coffee table that either of them seemed to notice him. He had his back turned to them both, only a couple of feet away from where they were sat at opposite ends of the couch. Sam was first to make a comment. “You’ve missed a spot, Dean,” he said sternly. “You need to get right down underneath the table and do the underside too.”

Grinning to himself so that they couldn’t see, Dean bent down further and made sure to stick his ass out as he reached the duster underneath the table. The motion made the dildo jab into his prostate again, and he bit his lip to keep from crying out as he gave a deliberate wiggle of his hips.

Cas and Sam had both looked up to watch him, and they exchanged a brief glance with each other as they enjoyed the view. Dean’s balls were visible between the part of his thighs, and they could see the way the end of the dildo shifted with each movement. They knew how much this must be tormenting him.

“Come here, Dean,” Sam said after watching him for a couple of minutes. “Give me that and let me take a look at you.”

Dean turned around as Sam leaned forward to take the feather duster off him, and then stood back for them both to take a look. His face felt hot again and his cock would have twitched if it wasn’t so weighed down.

Sam smirked as he extended the duster and lightly tickled it over Dean’s knees, pressing between them to indicate for Dean to spread his legs wider. Dean obliged as Sam started to trail the duster up the insides of his thighs, and he held his breath as he tried to resist squirming. They knew he was ticklish.

Sam continued to drag the feathers lightly over the sensitive skin towards Dean’s crotch, loving the way Dean’s lip whitened as he bit down on it hard. By the time the duster crept under the hem of the apron, Dean finally lost control and let out a noise that was somewhere between a moan and a giggle. Sam flicked the duster against Dean’s balls, grinning at his brother’s reaction. “Do you like that, Dean?”

Dean nodded silently, not trusting himself to speak.

“Do you think this is a better use for it than dusting?”

“Yes, Sammy,” he just about managed to squeak, which caused Sam’s grin to widen.

“Well, I think it’s very useful for dusting. You look very pretty when you’re using it, with that plump little ass sticking out and wiggling at us. You know I’ve been videoing it, don’t you? It drives me crazy. Turn round and I’ll show you want it makes me want to do.”

Sam whipped the duster out from between Dean’s legs as Dean did as he was told, and then the younger Winchester suddenly grabbed his brother’s hips and pulled him towards him. The next thing Dean was aware of was a sharp pinching sensation as Sam planted a firm bite on his left ass cheek. He yelped.

“Mmm, delicious,” Sam mumbled against his skin, and then pulled his mouth away and rubbed a soothing hand against the marked flesh. “You need to stop being so distracting.”

Cas had been watching them and now seemed to want his own turn. “Get over here, Dean,” he commanded, and then Sam picked up the duster again and slapped it against Dean’s cheeks as he turned to cross over to Cas. “That dildo looks like it’s slipping,” the angel growled, reaching up to grasp Dean’s hips and then pulling him roughly forward so that he ended up straddling Cas on the couch. Dean felt the movement inside him as Cas reached up to firmly grasp the end of the dildo, and then started to pump it shallowly in and out of him.

Dean gasped, pleasure beginning to fill his ass while the pressure around his cock increased. He knew he wasn’t going to get to come, not properly with his cock plugged and locked up, and he didn’t know how much of this he could take. “Cas, please…” he whimpered as the thrusts began to get faster and deeper. “Sammy put it in, he’s the one who’s meant to take it out…”

“I’m not taking it out; I’m adjusting it,” Cas replied simply, his free hand going to cradle the back of Dean’s head where it had collapsed against his shoulder.

“Besides, Dean, I’m filming it,” Sam said, and a quick glance sideways told Dean Sam had gotten his phone out again. In the back of his mind, Dean wondered what kind of video all this was going to make. Part of him was curious to see it and know what he looked like to both of them, but right now he was too distracted by the sensations filling his ass.

“ _Fuck_ _fuck fuck…”_ he moaned softly, burying his face in Cas’ shoulder as he felt his balls swelling painfully and straining for a release they couldn’t possibly have. If his cock hadn’t been stuffed up it would have been leaking semen by now, and every thrust of the dildo made the pressure grow more uncomfortable.

By the time Cas stopped Dean had almost completely collapsed on top of him, his legs reduced to jelly. Dean felt Cas give one final thrust to push the dildo firmly and deeply into his ass, leaving just the couple inches of base resting outside his hole. “I think that should stay in now,” Cas stated, trying to help Dean to his feet again, who just about managed to hold himself steady. His balls were still swollen and he was even more frustrated than before, but he knew they were going to make him wait. “Don’t you have some work to be getting back to?”

Dean nodded as Sam put his phone away again and pushed the duster back into Dean’s hand, having finished teasing him.

“Come find us when you’re done,” Sam said dismissively, settling himself back down onto the couch and staring at Dean expectantly.

Dean bit down his frustration and tried to ignore the ache between his legs, intending to just get on with this so they could get back to playing with him as soon as possible, but it seemed they weren’t quite done. Just as he was about to turn away and start getting to work again, Sam suddenly grabbed hold of Cas and pulled him down on top of him as they both collapsed onto the couch, aggressively devouring each other’s mouths.

Dean stared. That was the last thing he’d expected them to do, and he felt his cock give a futile throb of arousal while a pang of jealousy stabbed in his gut. They were making out as if he wasn’t even there.

For a moment or two longer he stood simply gazing longingly at them, hoping they’d take pity on him and invite him to join them, but as Sam cast a cursory glance at him all he said was, “The sooner you finish your chores, Dean, the sooner you can have some fun.”

Dean swallowed, trying to force down the jealous tears that he could feel threatening to spill as he turned his face away. He wasn’t being fair. He knew he wasn’t. This was completely irrational and after all the attention they gave him they should be allowed to have some fun by themselves, but he still couldn’t help how he felt. Especially not after the way they’d just teased him.

Somewhat sulkily, he stalked out of the room – or stalked as best he could with a giant dildo in his oversensitized ass – to find somewhere else to clean and leave them to it. He didn’t want to have to watch if he couldn’t join in.

Both Cas and Sam waited until Dean had left before they drew back from each other, Cas staring down at Sam with a look of concern. “Do you think we upset him?”

Sam looked anxious for a moment, but then dismissed it. “Maybe a little, but we’ll make it up to him later. That’s all part of the reward.”

“Alright. I know he’s a masochist, but I feel kind of mean…”

A guilty look had settled on Cas’ features as he avoided Sam’s gaze, and Sam raised a hand to gently caress the side of Cas’ face and tilt his chin towards him. “Hey, he’s been wanting us to get along for years, and I know he may pout about this for a bit at first, but deep down he’s happy. You should have seen the look on his face while he was watching us.” He raised his head upwards then to press a gentle kiss against Cas’ lips. “This will work, Cas. For all of us. I promise.”

His reassurances seemed to work for Cas, who smiled. “I know. I believe you. We’ll blow his mind later on.”

“We will,” Sam agreed with a grin, his hands going to Cas’ crotch and trying to work his zipper down. “Now, come on. If we’re keeping Dean’s dick locked up I’d love to have a play with yours…”


	21. Chapter 21

**Summary for the Chapter:**

> Kinks: voyeurism, dildos, anal play

The bunker was huge. Of course it was; that was the whole point, because there was no way in hell Dean was going to be able to clean it all in a day. Or in two days. Or three, even. Nor did he particularly want to, but that was exactly why they made him do it. He was still pouting as he tried taking the duster around the main hall, finding this ten times less fun without Sam and Cas there watching, but If he wanted the treat from them afterwards he knew was going to have to earn it. A more fun way of earning it, he thought, would be if they just let him suck them or finger them or do anything to get them off, but if he enjoyed it he supposed it wasn’t really a test.

By the time he’d been going for about three hours, he was utterly bored. Even the dildo wasn’t helping make the experience at all fun anymore, instead just making things more difficult as he constantly had to clench his ass cheeks together to keep it from slipping out. He wished they’d just fucking belted it in. It was an unwelcome distraction that grated on his nerves, and what made things even more annoying was that he needed to piss now too. He’d had enough. He was going to have to go find Sam and Cas and get them to do something.

They weren’t in the lounge when he checked. Nor were they in the kitchen, and it only worsened his mood further when he guessed that they must be in one of the bedrooms. Having sex without him, no doubt.

Dean went to check his bedroom first – the one they normally slept in – and finding it empty he went to try Sam’s next. Sure enough, as he approached he heard the sounds of delighted moans drifting through the partially open door. Trying to hide his scowl, he gently pushed it open further to see what was going on inside.

As the door swung back it revealed Cas lying flat on his back on the bed, knees in the air and spread wide apart to make room for the brown-haired head between them. Sam was currently licking Cas’ balls, and Dean watched with growing jealousy as his brother’s tongue moved to run up Cas’ length and then Sam closed his entire mouth round the head of the angel’s cock. Cas moaned in pleasure.

Neither had noticed Dean standing in the doorway, far too distracted as they were, and he tentatively knocked and cleared his throat to get their attention.

At the noise, Cas’ eyes flickered in his direction. Sam carried on as if Dean wasn’t even there. “What is it, Dean?” Cas asked breathlessly, still caught in the throes of pleasure from Sam’s mouth between his legs.

Dean blushed, feeling glad that he’d distracted them and at once guilty for feeling that way. “My dildo is slipping and I need to piss,” he stated simply, getting to the point.

A look of irritation flashed over Cas’ features, as if he wished he could just focus on Sam’s sucks and not worry about Dean. “Can’t you just hold it in?”

“I’m trying, Cas, but it’s difficult.”

The angel sighed. “Alright, come here,” he said with a wave of his hand. “Show me your ass.”

Dean went to stand beside the bed, turning to present his ass cheeks to Cas, who reached up to grab the end of the dildo protruding between them and gave it one quick shove back into Dean. Dean’s breath left him in a sudden burst and he tensed for more, but much to his disappointment, he didn’t get any. There was to be no repeat of earlier.

“Any better?” Cas asked as Dean turned around again.

“Yes, Cas, thank you. But I still need to piss.”

Cas shut his eyes and let his head flop back down onto the bed. “Do you want to take him, Sam?” he grumbled.

Dean heard the wet pop as Sam slid off of Cas’ dick. “Dean, I’m busy sucking Cas right now. Are you alright to wait?”

Dean nodded obediently. “Yes, Sammy.”

“Alright. Stand and watch, if you like. I think I’m almost done.”

Dean did. Despite the jealousy burning in the pit of his stomach, when he reassured himself that he’d get his turn eventually this was really fun to watch. Of course he thought they were both fucking hot, and the expressions on Cas’ face as Sam wrapped his lips around the angel’s cock and swallowed it down were beautiful. Dean loved the little whimpers that he made, and he loved to watch the sight of Cas’ cock sliding in and out as Sam bobbed his head.

Just as Sam had said, he was close to finishing Cas already. Soon, Cas was balling his fists into the sheets and crying out as he came into Sam’s mouth. Sam licked it all up and then pulled his mouth away. “You alright, Cas? I’m just gonna take Dean to the bathroom, then I’ll be back.”

The angel nodded his fucked-out acknowledgement and then Sam stood up.

“Alright, Dean. Come on,” he said, pulling the duster from Dean’s hands and putting it down beside Cas before pulling his brother back out into the hallway. Dean noticed there were still a couple of pearly drops of come glistening on Sam’s lips, and he couldn’t help but stare.

Sam noticed, and chuckled slightly. “You want to try some, don’t you?”

Dean nodded.

“Well, let’s see if you deserve it. How much cleaning have you done?”

“I’ve finished the lounge, the kitchen, and I’ve started the entrance hall.”

Sam seemed satisfied. “Good enough. Come here.” He placed a hand on Dean’s neck and dragged him forward into a kiss, roughly tangling their tongues together as Dean tried to lick up the last of Cas’ come. There was a trace of the angel’s salty taste as the drops hit Dean’s tongue, and he smiled.

“There,” Sam said, pulling back again. “Now you said you needed the bathroom…”

Once they’d reached the toilet, Sam popped out the penis plug, hitched up Dean’s apron and pointed his dick towards the toilet bowl. It was just as Dean began to piss that Sam made a further comment. “Is everything okay with you, Dean?”

“Yes, I’m fine, Sammy,” Dean lied, not wanting to have this conversation while piss was streaming out of his slit.

“Are you sure? Because you seem upset about something?”

“I’m fine,” Dean insisted again. He finished pissing and Sam shook him off before rearranging his apron back over his crotch.

“You know I love sucking your cock, right?” Sam said as he went to wash his hands, correctly guessing the cause of Dean’s bad mood. “But you understand we have to keep it locked up right now, or you’d never appreciate it when we _do_ suck it. That’s why when I wanted some cock earlier, Cas let me have his. It’s not because we don’t think you’re any fun anymore, Dean.”

“I know, Sammy,” Dean mumbled, feeling ashamed by his own reaction. He did know that, in a very objective and detached sort of way, but his emotions weren’t so easily reasoned with.

Sam patted his shoulder reassuringly as he led Dean out into the corridor again. “Don’t worry. When you’ve finished all your chores we’ll get that gorgeous cock of yours out again and have plenty of fun with it.”

“It’s gonna take me a while.”

“I know. It’s okay, we aren’t expecting you to do it all in one go. Have you had enough for today?”

Dean nodded. On the one hand, he knew the quicker that he got everything done, the quicker they’d take his cock out of the cage again, but there were other kind of fun they could have with him and he’d already grown bored enough. “Am I stretched out enough for you and Cas, yet?” he asked, trying not to sound like he was pleading too much.

Sam smirked. “Let’s see,” he said, before grabbing Dean’s shoulders and spinning him round to slam him up against the wall. Dean’s cheek collided with the plaster and he felt Sam’s foot between his ankles pushing them apart. Then, with Dean’s legs spread wider, Sam grasped hold of the end of the dildo and yanked it out.

Dean whined, feeling a sudden thrill rush through him, and then he heard the wet sound of Sam spitting on his fingers before reaching down to push two of them insistently into Dean’s hole. Dean’s muscles clenched in shock, but he let out a sigh of relief. Yes. This was what he wanted. Something warm moving inside him and carefully rubbing him the right way rather than just cold plastic.

Sam teasingly brushed a fingertip over Dean’s prostate, triggering a soft moan, and then added another finger. He steadily worked it inside, listening to the way Dean’s breathing became faster and rougher with each movement, and then tried to add a final finger. Dean clenched tightly around him as a shaking gasp escaped his mouth.

Suddenly, and much to Dean’s dismay, Sam pulled out again. “You’re still resisting me when I try and get all my fingers in,” he said bluntly, wiping his fingers down on Dean’s apron. “You’re not ready yet. Give this a couple more hours.” He repositioned the dildo at Dean’s entrance and steadily pushed it back in. Most of the lube had long since rubbed off, and Dean grimaced in discomfort. “It’s up to you what you do now. You can carry on with your chores or take a break for a bit.”

Dean nodded disappointedly. “I’ll carry on with my chores,” he replied, guessing he may as well get as much done as he could.

“Good boy, Dean,” Sam said, looking pleased with his choice. “I’m looking forward to getting your cock out again. Now go get your duster off of Cas and check back in with us in an hour or two…”


	22. Chapter 22

**Summary for the Chapter:**

> Kinks: sex on camera, facials, creampie, rope bondage

Two hours later, and Dean’s endurance had reached its limit. Fortunately for him, neither Sam nor Cas seemed inclined to drag this out any longer. The minute he’d gone to find them in Sam’s room again, he hadn’t even had to say anything before Cas had ripped the apron off him then impatiently shoved him down face-first onto the bed. Dean let out an “umph” as he collided with the mattress, and then he felt Sam’s hands dragging his own wrists up towards the headboard and securing them in place with a necktie. His shoulders protested, but his cock gave an excited twitch within its confines.

The next thing he was aware of was the firm grip of hands on his ass cheeks, spreading them apart, and then the thick length of the dildo was sliding out of him. Dean sighed as he felt the hunk of plastic finally leave his body, and as he opened his mouth another piece of plastic was suddenly forced into it. His breath caught and he nearly choked on the gag for a moment, but then relaxed and inhaled deeply through his nose as he allowed the ball gag to be positioned and strapped in.

“Bet you’ve been longing for this all day, haven’t you?” he heard Cas say from behind him, the angel’s voice a low and husky growl. “Having that dildo up there to tease you and torment you and stretch you out…Bet you couldn’t wait for us to get rid of it and stuff a real cock inside you instead.”

Dean nodded emphatically, moaning around the ball gag as he tried his best to beg without words. He probably looked pathetic, but he thought they’d like that.

“You little slut,” Cas growled. “Time to see how open you are…” Cas suddenly thrust three pre-lubed fingers into him in one go, and Dean whimpered. His hole was already pretty well-stretched, eagerly opening up to accept the intrusion. “Oh, you’re just _gaping._ Begging to have a cock up there…” Cas breathed, adding a fourth finger and curling them a couple of times before sliding back out. A moment later, Dean felt the warm, thick head of Cas’ cock nudge at his entrance.

He whined, lifting his hips slightly to push up against Cas and invite him inside. The angel held back a moment longer, and as Dean twisted his head to the side to try to see what was happening, Sam stepped into view.

The younger Winchester was completely naked, and Dean’s eyes panned up appreciatively over the toned muscles of his thighs and torso towards his face. It was impossible to miss his cock, which was hard and leaking just a short distance above Dean’s head, and Dean felt his own dick give a futile throb at the sight. Having cast a cursory glance over the rest of Sam’s body, Dean couldn’t help but hone in on it again, watching as a bead of precome collected at the tip and then dripped down onto the bed.

Sam grinned down at him, relishing the hungry look in Dean’s eyes. Part of him wished they’d left more of Dean’s holes available, but if Sam were to use them, he’d be less able to do what he was doing now. His left hand was closed firmly around the base of his cock, leisurely stroking himself, while in his right he held a video camera that he panned up and down the length of Dean’s body, taking care to capture every gorgeous inch of him. “I’m getting all of this on camera, Dean,” he said with a salacious lick of his lips. “Want you to watch this back later and know how hot you look; how amazing your body is when it’s opening up for us. You’ll get to see Cas fucking you. Isn’t that exciting?”

Dean stared up at him, breathing coming heavy as his heart pounded in his chest. Part of him was terrified at the thought of watching this back and realising just how needy and pathetic he actually looked…but at the same time, he was hopelessly turned on. His cock ached, straining to get hard while his balls begged to release their load, but he was all locked up. The best he could hope for was that they’d let him orgasm but not ejaculate. That could hurt, but it would be worth it if Cas would just get on and fuck his ass already.

A smirk spread over Sam’s lips, and Dean watched as he turned the camera to point at Cas, focusing on where the angel was lined up at Dean’s hole. Firm, rough hands closed around Dean’s hips, and then with one hard thrust, Cas slid home.

Dean’s scream was muffled by the gag, but the plastic ball couldn’t hide just how desperate and needy and _ecstatic_ the sound was. Dean pushed his hips firmly upwards, forcing Cas deeper inside, and then the angel slammed him downwards again with his next hard thrust. A frenzied blur of thoughts to the tune of _yesyesyesyesyes_ cascaded through Dean’s mind, leaving his mouth in a series of muffled moans. _This_ was what he wanted: Cas’ warm, hard length inside him and moving with purpose rather than just a piece of cold plastic constantly slipping and tormenting him. His cock wanted to respond and stand up tall with joy, but the most he was going to get was a throbbing tightness inside the cage.

Still, for now this was enough. Dean grunted with each thrust Cas made, feeling them get faster and rougher and deeper as he heard the slap of Cas’ balls connecting with his skin. All the while Sam stood filming, a wicked grin on his face and left hand pumping himself furiously.

When Cas came, after what Dean thought was after nowhere near long enough, multiple tremors racked Dean’s entire body as he felt each hot spurt inside him. He cried out and shuddered, his own cock giving a painful throb, and then felt Cas’ weight collapse down on top of him. Off to his right, Sam had captured the whole thing on video, and was still jerking himself as he zoomed in on Dean’s face. He directed his cock downwards slightly to point at Dean, and Dean realised what was about to happen a moment before Sam grunted and came. The warm, viscous liquid landed on Dean’s face in several pulses, and Dean blinked and moaned as he felt it coat his cheeks and get caught in his eyelashes. A significant amount landed on his lips, and he bit down on the gag in frustration that he couldn’t lick it away.

He was still fucking horny, and in his forlorn desperation he gave a wiggle of his hips to try and grind his cock down into the mattress, but of course it felt of nothing. Resigned, he let out a breath and allowed his muscles to go slack, hoping his cock would cease its efforts to get hard soon and just accept its fate. This was too damn frustrating.

Sam crossed over to him, making sure to get one last shot of his come-coated face before shutting the camera off and setting it to one side. “You looked so fucking incredible, Dean,” he said hoarsely, reaching down to wipe a drop of come from Dean’s brow that was threatening to run down into his eye. Then he leaned over him to unfasten the gag and pull it from Dean’s mouth. Dean found he was eye level with Sam’s gradually softening cock, and as the plastic was removed from his mouth, he felt an urge to lean in and try to lick it. He couldn’t move fast enough, however, before Sam had stood up out of reach again. A moment later, and Dean felt Cas clambering off of him and going to stand beside Sam.

“Did you get all that?” the angel asked.

Sam nodded. “Every second.” He flashed a grin at Dean. “Don’t you have something to say now, Dean?”

“Thank you for fucking me, Cas,” Dean answered obediently. “And thank you for filming it, Sammy.”

“Are you looking forward to watching it later and seeing what a little slut you are?”

Blushing bright red, Dean nodded.

Sam’s grin widened. “I should show you what a puffy hole you have now too.” He then vanished from sight again, picking up his phone as he switched back to taking still pictures, and moved behind Dean to take a photo of the swollen pink pucker visible between Dean’s cheeks. Utterly embarrassed, Dean turned his face to bury it in the mattress, causing most of Sam’s come to rub off onto the sheets. He didn’t mind them staring at his body one bit, no matter how invasive or thorough the inspection, but for them to keep a permanent record of it set nervous butterflies fluttering in his stomach.

“Here, Dean,” Sam said, holding up the phone screen for him to see. “That’s what you look like.” Dean gritted his teeth and forced himself to look. His hole was as red and puffy as it felt, and he could feel as well as see that some of Cas’ come had spilled out of him and was dribbling down his thighs. His face burned bright red, but a glance at Sam and Cas’ faces told him they were very happy with the sight.

“Just fucked, and still looking so fuckable,” Cas commented with a grin, exchanging a glance with Sam.

“Well, it’s still early,” Sam replied, tongue running smoothly over his lower lip. “I don’t think we’re quite done with that gorgeous hole yet. Dean, we’re going to turn you over.” He and Cas started undoing the restraints on Dean’s wrists in order to flip him onto his back, and Dean felt his heart rate begin to increase again. “And then we’ve got a few more things that we’d like to put up there and play with.”

Dean swallowed as he was repositioned, and offered up his hands again to be restrained. “What would you like to put inside me, Sammy?” he asked shyly, spreading his knees as far apart as possible to make sure they could access his hole. It was a little sore from the fucking he’d just had and the entire day of stretching, but he wasn’t about to say no to having them play with it more.

“You’ll find out soon enough,” his brother answered, grasping Dean’s knees and pushing them towards his shoulders so that his ass stuck up in the air. “Now hold still while we tie you up.”

Dean’s stomach did a backflip at those unexpected words, and then he noticed that Cas had retrieved a ball of rope from somewhere – or rather, soft cord, so it was less likely to chafe – and was about to use it on him. He obediently held still while they began to tie him up, working a series of knots along his arms, under his shoulders and then across his chest.

“Lean up,” Cas instructed, and Dean did so to allow Cas to pass another length of cord beneath him and then repeatedly loop it back over his chest. After doing that several times, Cas straightened up and gazed down at Dean with a sincere expression. “I’m going to ask you to breathe out now, Dean, and then I’ll ask you to breathe in a little so I can tighten the rope to restrict the maximum amount of air you can inhale. Are you comfortable with letting me do that?”

Dean gulped, meeting the angel’s eyes as he stared steadily up at him. It was rare that they did breathplay. Very rare. It was one of the few things that had caused Dean to genuinely panic in the past, but on the last few occasions he’d been okay. The restricted breathing he could handle, as long as they weren’t actually blocking his mouth or throat.

He took a moment to consider while Sam and Cas patiently paused to let him answer, but Dean honestly couldn’t see himself declining this. All things considered, he thought he’d be fine. “Yes, Cas,” he answered with a nod. “I’m okay with it.”

“Alright then. Breathe out then in again, until it’s comfortable.”

Dean did so, drawing in about half a lungful of air and holding it as Cas tightened the cord about his chest. “How’s that?” the angel asked, testing the knots, and Dean exhaled before trying to draw air fully into his lungs. As expected, he felt the rope cutting across his ribs and compressing his diaphragm on the inhale, but he could breathe enough to be comfortable.

He nodded. “That’s fine. I’m good.”

Satisfied, Cas and Sam resumed tying him up, this time making knots that passed around his ankles and thighs to keep his knees bent. From the bindings on his legs, they then looped the cord back to fasten it to the ropes on his forearms, ensuring he was rendered nearly immobile and his legs and ass stayed up in the air.

“Alright,” Sam said once he was fully secured, running his eyes over Dean’s body. “You okay with that? Anything you want adjusting?”

Dean wriggled a little to test the ropes and then shook his head. “No. It’s all good.”

“Not cutting off circulation anywhere? You can move your fingers okay?”

Dean tested it. “Yep.”

Sam nodded. “Okay, then. We’re going to put the gag back in now. If you want us to stop at any point, use the signal.”

Dean nodded his understanding as he opened his mouth wide again to allow the ball to be placed back in, feeling a hot flurry of excitement growing in the pit of his stomach. A fresh thrill washed over him as Sam finished securing the gag and went to stand in front of Dean’s exposed ass, while Cas bent down to retrieve something from under the bed. What he pulled out transpired to be a box, which Dean assumed must have all their toys in it. His cock gave a frustrated, useless throb.

“Now then,” Cas said teasingly as he slowly removed the lid, making sure to meet Dean’s gaze as he revelled in how utterly helpless the hunter looked tied up before him. “Let’s see what fun things we have in here…”


	23. Chapter 23

**Summary for the Chapter:**

> Kinks: anal beads, stir sticks, facials, felching, prostate milking

Castiel produced the first item slowly, raising it high in the air so that Dean could see it. It was a string of six purple plastic beads that grew progressively larger along its length, and Cas held it by the smallest one so that the largest one dangled down and gave small, pendulum-like swings at the end. Dean stared. He knew where those beads were going, and although the first three looked a reasonable size, the final ones were intimidatingly large. Instinctively, he clenched his hole at the sight, and heard Sam chuckle.

“You’ll want to keep nice and relaxed for this,” his brother said, raising a finger to gently rub around Dean’s hole. He didn’t try to press inside, but teased at the ring of muscle to help keep Dean open. “Would you like us to put these inside you?”

Dean gulped, nervously wondering how much the beads were going to stuff him up, but he was definitely keen to find out. He nodded.

“Would you like to do the honors, Cas?” Sam said, and then Cas stepped forward to lower the beads to Dean’s entrance.

“It would be my pleasure,” the angel replied with a gleeful grin, and then pushed the smallest bead into Dean’s hole. It went in easily, Dean’s body readily opening up to accept the small sphere. His channel was already coated with lube and come and there was little friction, but he thought he heard a quiet, wet suctioning sound as the bead slid inside. It tickled, almost, as the tiny ball slipped past his rim, and Dean’s breath hitched. He could feel the weight of the other five tugging at the bead inside him, pulling at his rim and just threatening to cause it to pop out again. Cas soon averted that as he raised the second bead to rest against Dean’s entrance, and then firmly pushed it inside.

Dean felt that one more keenly, the width of it stretching him out a little more, and he felt the bead already inside him bump and shuffle along his channel as the second one was added. He let out a slow, steady breath.

Cas raised a hand to rest on Dean’s thigh and gently rubbed at a strip of skin between two lines of rope. “Ready for more?”

Dean grunted his affirmation.

Grinning, Cas lined up the third bead. This would be the one where Dean would start to truly feel it, leaving him with a significant mass of plastic inside him. Cas gave it a push with his index finger, feeling greater resistance from Dean’s body before the ball’s circumference breached him and the rest was sucked inside. Cas gently rubbed against Dean’s clenching hole as it closed up again, giving time to adjust. “Can you feel yourself getting full up, Dean?”

He glanced up at Dean’s face from between Dean’s legs, and saw Dean give the tiniest of nods.

“Well, we know you’ve got more space inside your ass than this. Ready for the next one?”

This time, Dean’s nod was larger. Even with a lump of red plastic stuffing up his mouth, he still looked thrilled.

Cas pushed in the fourth bead. He had to give it a hard shove, pushing the others out of the way as well as making sure Dean stretched out enough, and the action appeared to cause something inside Dean to strike his prostate. He grunted sharply, eyes fluttering shut, and his hips jerked against their restraints.

Cas grinned. “You like that?” he teased, giving a tug on the string to pull the last bead back out again. Dean grunted again as it left him, and then once more as Cas repositioned it and shoved it back in. Dean looked utterly, beautifully depraved like this: lewd moans rumbling in his throat, eyelashes fluttering on freckled cheeks, crinkles forming at the corners of his eyes as he screwed them shut…all because of the pleasure he felt at having things inserted into him. Cas licked his lips as he tried to imagine what Dean’s cock would be doing right now if they hadn’t bound it and plugged it up. Just by looking at his balls, Cas could tell how swollen they were. He’d have to talk to Sam about milking him at some point before the cage came off.

Right now, all he was concentrating on was getting the rest of the beads inside. He was on the fifth one, almost two inches wide, and Dean’s body didn’t want to take it easily. Dean moaned and huffed as Cas tried to push it in, and eventually he got it far enough inside that Dean’s hole closed up again behind it. All but the final bead jostled inside him, and Dean grunted as he felt the uneven shapes bump against his walls and strike his sweet spot.

“Just one more to go now,” Cas said, lining up the final bead and starting to ease it in. The noises Dean made were utterly delicious as Cas’ movements pushed around the plastic balls already inside him, taking up room, and then he worked the last one in past Dean’s rim. It popped out again almost immediately, making Dean squirm as his hole was stretched and closed and stretched again in quick succession, before Cas gave the bead another push far enough to allow Dean’s clenching to keep it inside.

The angel stepped back, staring down at nothing but the ring at the end of the string hanging down from Dean’s hole. “Perfect,” he announced in satisfaction. “Are you all stuffed full now, Dean?”

Dean cracked his eyes open to look at Cas and nodded.

Cas tsked at him. “No you’re not; not quite. Sam, is there anything you’d like from the box?”

They switched places, Sam coming to stand between Dean’s legs, and Dean felt his stomach do a backflip as he realised they were going to put even _more_ up there. “Hmm, let’s see,” Sam said as he rifled through the contents of the box for a few seconds, and then took out two plastic sticks with tiny discs on the end. Dean swore they were coffee stirrers. “Let’s try these. No point having all those beads up there if we’re not going to move them around a bit.”

Dean whimpered as he felt Sam’s fingers press into his hole to hold the beads in place while he pushed the end of the first stirrer in, and then he let Dean close up again. He began to ease the plastic rod further inside, and Dean bit down hard on the gag as he felt jolts of pleasure shoot through him. The beads rubbed at his prostate, over and over, with every move of the rod Sam made, and Dean felt a painful, aching pressure growing in his balls and straining his cock. He just wanted release. It was almost cruel that they were doing this to him without taking the cage off, but he knew he’d have to be patient. For now he’d just take what he was given, and hope they weren’t too merciless in their teasing.

Holding the stick in place with one hand, Sam went to pick up the other and then began to insert that inside Dean too, steadily starting to thrust with it. It felt like bolts of electricity shooting from Dean’s ass all along his spine to his brain with each jab of the rod. He was stuffed so full and there was so much movement inside him, hitting his walls in so many different places with different pressures and it was setting his nerves on fire. He wanted so badly to come, but the ache just kept building and building with no means of release. If the gag hadn’t been in place, he would have been begging by now.

Sam kept going for what felt like a torturous age before Cas made another comment. “He’s looking very strained, Sam. Do you think we should do something about that?”

Dean held his breath, hardly daring to hope that they might allow him some relief.

“Hmm,” Sam said contemplatively, stilling his motion for a moment. “You’re right, his balls are looking very full. No point leaving him in this state. Maybe we could ease that up a little bit.”

“Alright,” Cas said, going to stand beside Dean and raising a finger to trail lightly down the side of his face. With his other hand, he reached down to Dean’s caged cock that was resting against the inside of his thigh. “Dean, I’m going to take your plug out now,” he explained, pinching the plug protruding from the end of the cage. “Let you relieve some of that pressure, but you don’t get to come today. You need to be a good boy and wait.”

Dean’s eyes were watering with frustration and aching need, but that sentence held a promise that he’d get his reward eventually, and so Dean gave an obedient nod.

Cas popped out the plug, and immediately a few drops of clear liquid dribbled from Dean’s slit. Sam resumed moving the beads while Cas’ hand went to Dean’s balls, gently massaging them to encourage more fluid to spill. Dean sighed. It was infuriating that he’d get no more than this, but it felt good. Cas’ touch was tender on his aching balls and it was such a relief just to have them not feel so full, feeble pulses of seminal fluid dribbling out of him each time Sam managed to strike his prostate.

When they finally thought he was milked enough, so that Dean could feel a wetness running down his right thigh, Cas took hold of his caged cock and plugged him back up. Sam steadily slid the stir sticks back out one by one and then grasped the ring at the end of the bead chain. “Okay, Dean, I think that’s you almost done,” he said, and then proceeded to pull the beads out with one long, steady tug.

Dean moaned a little when the first two stretched him out, but by the time the last one left his body he was left feeling a hollow, empty ache. He’d gotten so used to having something inside him that it felt wrong to having nothing there.

“Did you enjoy that, Dean?” Cas asked as he began to unfasten Dean’s gag, allowing Dean to speak to answer.

Dean flexed his jaw as the gag was pulled away followed by a string of drool. Part of him wanted to say, “Yes, but you’re both really fucking mean for not letting me come and can you just get rid of this fucking cage and jerk me off,” but he didn’t want to be rude or ungrateful, so instead, he nodded and replied, “Yes, Cas, very much. Thank you both for playing with me.”

Cas smiled and wiped some spit from the corner of Dean’s mouth with his thumb. “Do you like having things in your ass?”

“Yeah. A lot.”

“Good,” Dean heard Sam say, and then he looked up between his legs again to see Sam lining up his erect cock at Dean’s already worn-out hole. Sam smirked as he saw Dean’s surprised look. “What? Didn’t think we spent all day stretching you out just to have Cas fuck you? I’m getting in there too.”

Dean licked his lips. He wanted Sam inside him, but his hole was definitely more than a little sore by now and they’d spent all that time milking him only to let his balls get uncomfortably full again.

Sam noticed his apprehension. “You’re alright with that? I don’t want to fuck you if you’re too sore.”

Dean immediately gave an enthusiastic nod. “Yes, please fuck me, Sammy.”

“Alright,” Sam replied with a grin, pushing his cock up against Dean’s gaping entrance so that just the head slipped inside. “Honestly, you got me so hard just letting me play with your hole that I don’t think this is gonna last that long.” Then, he pushed himself the rest of the way inside.

Dean gasped and grunted as he felt his brother begin to thrust, teeth descending to bite down hard on his bottom lip, but Cas immediately put a stop to that. “Open your mouth, Dean,” he ordered as he started to pump himself right beside Dean’s head. “I want you to taste this when I’m done.”

They finished in an almost perfect inverse of earlier, Sam thrusting his hips hard into Dean until the friction finally pushed him over the edge and he spilled himself into his brother.

Dean’s ass clenched as he felt the heat of it inside him, holding Sam in place a moment longer before Cas finished himself with a yell. He came all over Dean’s open’s mouth, coating his cheeks and lips with a salty white cream that Dean eagerly tried to lick up. Once he’d swallowed as much of it as he could, Cas leaned down to help him, licking up the drops he couldn’t reach and then pressing his mouth to Dean’s in a deep kiss.

While their tongues entangled, Dean felt an unexpected but very _very_ welcome moistness between his legs as Sam pressed his own hot mouth to Dean’s hole. He began to lick up the come that was dribbling out of Dean, who moaned into Cas’ mouth from pleasure. This was filthy and wonderful and he loved having both their mouths on him like this.

It took some time, but once they both thought they’d managed to clear up as much of their come as they could, they straightened up again. Sam gave Dean’s ass cheeks a gentle rub as he stared down at just how pink and puffy Dean’s hole was by now. “Beautiful,” he remarked, and stared up to see Dean’s face blush a similar color to the one he was down there.

“I expect we’ve exhausted you by now,” Cas said as he and Sam began to undo Dean’s bindings, who replied with a rather tired sounding sigh.

“Yeah, but it was fucking worth it,” he mumbled, leaving out _but next time please touch my cock and make me come._

“Good,” Cas responded as he rubbed soothingly at the reddened rope indents on Dean’s skin. “Got to make sure you get plenty of rest now, though. You’ve got a lot of work to get through tomorrow if you want us to have some fun with your cock soon.”

It didn’t take long for them to get Dean completely freed again, and then they put the rope away and set toys aside for cleaning. Dean clambered up off the bed and flexed his limbs, stretching them out after spending so long bound in one position.

“How’s your ass doing, Dean?” Sam asked. “We wanted to plug you up afterwards, but you look like we’ve worn you out for one day.”

Dean clenched his cheeks a couple of times to test the soreness. True, his rim was stinging a bit (well, quite a lot) but it felt wrong to be so empty. “No, it’s okay, Sam,” he replied. “You can plug me up if you like.”

“Okay, lay down on your front then,” Sam said, taking out a butt plug from the box before sliding it back under the bed. He used the bottle of lube on the nightstand to prepare it while Dean reached behind himself to spread his ass cheeks helpfully. “Just a small one,” Sam said as he inserted it, “So it’s not too uncomfortable. How’s that?”

Dean had grimaced a little as it went in, but once in place he thought it felt okay. It wasn’t too big, but it was filling him up enough that it felt comfortable and familiar. “That’s okay. Thank you, Sammy.”

“Good,” Sam said, and gave Dean’s ass a brief rub to let him know he could stand up again. “Shall we go make you some dinner now? You’ve got to be hungry after all the hard work you’ve done today, and then you can go get some rest.”

Dean was, and that suggestion sounded great. He nodded. “Yes please.”

“Alright, Cas and I will just get dressed,” he said as he and then angel went to put their clothes back on. Dean felt a slight disappointment that their bodies were going to be hidden from view again, but after everything they’d just done, he couldn’t really complain. “You just hang on a moment, Dean, and then we’ll go get you something to eat.”

By the time they were heading to the kitchen, Dean was smiling with pleasure from the treatment his ass had just received, but with a newfound resolve to get all his chores done as quickly as possible, whatever it took.


	24. Chapter 24

**Summary for the Chapter:**

> Kinks: double penetration, special lube, oral sex

**Notes for the Chapter:**

> Hello again. I know it's been a very long time since I updated this, but I was /so close/ to finishing before my cardiophilia series suddenly kicked off and dragged my attention elsewhere. However, for the sake of closure, I would like to try and wrap this story up. We're almost there now. Just this and one more chapter.

Just as Dean had decided, he spent the entirety of the next day working to finish as many of his chores as possible. The only breaks he took were for Cas and Sam to feed him and take him to the bathroom when they said so. By the time their regular bedtime came around, he was still going, determined to get the whole thing finished as soon as he could.

In Dean’s room, Cas and Sam were lying in bed, waiting to see if he would join them. They didn’t keep a strict schedule, but by now they’d expected Dean would realise he ought to be going to bed and that they were expecting him. Still, both of them could hardly have failed to notice how hard he was working, and they both knew why. They decided to give him a few more minutes.

From opposite sides of the bed, Sam and Cas glanced over at each other. For a brief moment, it seemed that they were both contemplating saying something, but then they thought _to hell with that_ and simultaneously both rolled into the center to crash their lips together.

The kiss was fierce, Sam’s teeth nipping sharply at Cas’ bottom lip while Cas pulled roughly on Sam’s hair. Their legs tangled together, cocks rubbing over each other while fingernails clawed into each other’s backs. It was passionate, intense, and they both found themselves thinking they’d not done this together anywhere near often enough.

Sam moaned needily into Cas’ mouth, bucking his hips upwards as he sought more friction between their cocks, and Cas gasped and dragged his lips sideways to begin sucking down the column of Sam’s throat. Sam’s eyelids fluttered, contented sighs leaving his lips as he twisted his neck to expose more skin, but he then found himself staring over at an empty side of the bed. Cas must have noticed the way he seemed to deflate, the way Sam’s writhing became less desperate and wanton beneath him, and he pulled his mouth back to stare over in the same direction as Sam. “Something’s missing, isn’t it?” the angel remarked, before rolling off of the hunter.

Sam sighed again, this time less happily. “What time is it? We told him to come join us when he’s finished.”

“Almost ten thirty,” Cas replied, not even needing to glance over at the alarm clock. “You don’t think he’s still going, do you? We told him he wouldn’t get rewarded until he’d finished everything.”

A frown creased Sam’s brow. “It’s been three days. He’s done enough. I thought he’d have come to bed now.” That thought seemed to unsettle him, as a moment later he was standing up and pulling on a bathrobe. “I’ll go get him. We had plans for tonight, didn’t we?”

“I could go?” Cas offered, but Sam was already at the door.

“Nah, I’ll do it. You get everything ready,” and then headed off to find where Dean would be.

It was times like this Sam cursed how large the bunker was. He was already feeling mean that they’d told Dean he was supposed to clean all of it, without really considering just what that entailed or how thorough Dean should be. It took ten minutes of searching before Sam finally found his brother behind a stack of shelves in the library, dutifully still dusting.

“Dean, come on,” Sam said as he laid eyes on him, although he had to appreciate that he’d got a rear view of Dean’s bare ass with the dildo still implanted in it. “You must be exhausted. Come to bed.”

Dean glanced over his shoulder at him, and Sam could see he was looking fatigued despite the look of determination in his eyes. “I’m almost finished, Sammy,” Dean promised. “I said I’d get it all done.”

“Dean,” Sam said again, firmer this time, and his brother deferentially turned to face him. “It’s okay, you can stop.”

“You said you wanted me to do everything?”

“I know, but…we didn’t mean _literally_ everything, Dean. We were never expecting you to have to clean the garage, or the utility room, or every book in here or some other pointless thing… We just wanted you to do a bit of work and look cute shaking your ass while doing it. I’m sorry. That was out fault.” He looked genuinely apologetic. “We should have made it clear. Let us make it up to you. Come to bed. You’ve earned your reward.”

Even through his exhaustion, Dean’s eyes lit up. “You mean that?”

“Of course, Dean. Come here.” Visibly sighing in relief, Dean crossed over to his younger brother, who tugged off the now grimy apron and tosses it aside. “That’s not so cute anymore. Let me get a look at you,” Sam remarked, casting his eyes over Dean’s bare body and scrutinizing his now caged cock. “I think it’s time that came off. Shall we go find Cas for his key?”

It wasn’t not showing for all his tiredness, but Dean was giddy on the inside that the damned cage was finally going to be coming off. He didn’t think he’d get the rest he needed tonight unless he can finally release all that tension and get to come first. He was half excited and half just plain relieved as Sam lead him back to the bedroom where Cas was waiting for them.

“I was beginning to wonder if you were going to join us tonight,” the angel said as he saw they’ve arrived, but his had his key for the cage at the ready. “It would have been a shame if you didn’t. You’ve been so good, Dean; you’ve earned your reward.” Cas crossed over and kissed Dean gently on the lips, but then pulled back and gave him a once-over. “Although, are you sure you aren’t too tired? We could always wait for tomorrow…”

Dean shook his head fervently. “No, Cas. Not too tired at all.”

The angel smiled. “That’s good to hear. Now let’s get to that pretty cock of yours…” He slid his key into the lock to snap it off, and then handed Dean over to Sam to remove the other one. The younger Winchester was slow, almost cruelly teasing, as he removed the cage and slid Dean’s cock out. It hung limply between Dean’s legs for a moment before a quick tug from Sam had it rapidly filling. Both Sam and Cas grinned. “That’s really looking ready for a treat,” Cas said, before moving behind Dean and giving his bare ass cheek a slap. “But what about this part of you? We’ve been stretching it out for a long while now. I hope it’s adjusted.” He leaned over Dean’s shoulder to whisper in his ear as he slid the dildo out. “What do you think, Dean? There’s some things we’d like to put up there.”

Dean shivered. The feeling of the cold, hard length slowly exiting his body was such a relief for the muscles that had spent three days clenching to hold it in, but if Cas was offering to stuff his ass again…well, Dean didn’t want to turn that down. “Like what?” Dean asked shyly, and he could see Sam grinning at him.

“Like my cock,” Cas answered. “And Sam’s cock. Preferably at the same time.” Dean felt his stomach do a backflip. That explained why they’d spent so much time stretching him out. It was rare they both fucked him at the same time because it took so much prep and it left Dean’s hole sore, but when they did…just the thought of it had Dean’s head spinning.

He gave an emphatic nod of his head. “Yes. Please. Stuff me up nice and full.”

Cas grinned, pushing Dean down onto the bed so that he landed on his stomach, his now full cock trapped under him. “Gladly, Dean. Now let’s get you lubed up.”

Turning his head, Dean could see Sam go to fetch the bottle from the nightstand and then vanish behind him before the pair of them began to work his hole even more. Dean yelped as the first finger pressed inside him, unable to tell who it came from, but he realised almost immediately the lube wasn’t their regular kind. A tingling began to spread through his walls as the cold liquid was spread around them, and Dean gasped and wiggled his hips.

He heard the pair of them chuckle as his hole sloppily clenched around the intrusion, and then more fingers were added. Dean had to bury his face in the mattress to keep from moaning too loudly. The dildo in his ass had been a cold, inadequate mimicry of what he really wanted, but _this…_ these were warm, attentive fingers, carefully stretching him further and making sure his prostate got the occasional rewarding poke, and judging by the angles they were tugging at, the fingers had to be coming from both of them. He had no idea how he was managing to not come already as he rutted his cock incessantly into the mattress, driven wild by the sensations in his ass.

Both Sam and Cas took their time, but when Dean was a suitably whimpering wreck, they both pulled back to admire their work. “Look at him, just so desperate to be filled up,” Sam remarked, drinking in the sight of Dean’s fluttering hole. “I think we should give him what he wants.”

Dean found himself suddenly being rolled over, picked up, and then manhandled until he was sitting in Sam’s lap, facing him, at the edge of the bed. His brother’s thick cock slid along his crack, put didn’t push inside just yet. “Make room for Cas, Dean,” his brother ordered, and Dean braced his knees either side of Sam’s thighs and pushed up to allow Cas to get his slicked up cocked aligned at his hole beside Sam’s. Dean found himself staring into his brother’s eyes while he could feel Cas breathing heavily at his back. His cock gave a throb.

“You ready, Dean?” Sam asked breathily, and Dean was almost too giddy to even nod before he felt two cockheads pressing at his gaping entrance.

Sam’s just seemed to beat out Cas’ and make its way into Dean’s hole first, but Dean was just stretched so wide he eagerly swallowed them both up as Cas’ soon followed. The thickness of them both sliding up into him made Dean cry out, walls tingling from the lube and prostate rejoicing from the pressure. His cock twitched madly, dribbling copious amounts of pre-come onto Sam’s stomach before his brother grasped hold of Dean’s dick firmly to keep it under control.

Cas gasped, meeting Sam’s gaze over Dean’s shoulder as he felt the younger brother’s cock press against him deep inside Dean’s body. Dean was writhing over both of them, moaning obscenely, and as Cas snaked a hand around Dean’s hip to grasp onto his balls, the pair of them began to move. They set a pace to override Dean’s rhythmless wiggling, timing their thrusts together so that Dean was jolted forcibly upwards as he bounced on their cocks. Sam bit down on his own lip hard as he felt the friction on his dick, and he had to screw his eyes shut as he contemplated being this close to Cas as well as Dean made everything all the more perfect.

Both Cas and Sam’s hands were frantic, alternately tugging hard and fast on his cock and gently squeezing his balls before passing over to each other, ensuring Dean’s cock got all the attention it had been missing. Judging by the way Dean had thrown his head back, eyes tight shut and no longer even trying to keep his moans quiet, he was fucking loving it.

They hadn’t expected Dean to last long. They’d kept his dick caged far too long to think he could tolerate this for more than a few minutes, and as predicted, Dean was soon crying out and his dick twitching in their hands while he spilled himself over Sam’s chest. Even then, the pair of them kept going. They were far from finished, and Dean had to bury his face in the crook of Sam’s neck and bite down from the onslaught of sensations in his as. Both Sam and Cas had stamina, each of them grunting with pleasure and not letting up the furious pace as they both pounded into him. From the crazed assault on his prostate, it wasn’t long before Dean’s cock began to stir again.

Of Sam and Cas, the angel was first to come, biting down on Dean’s shoulder as his body convulsed and his spilled his seed inside the hunter. Sam felt Cas’ cock twitch, jerking against his own while Dean’s walls squeezed them tightly together, and almost immediately it tipped him over the edge to mingle his come with Cas’ deep inside Dean.

Dean whimpered softly into Sam’s shoulder as the pair of them slid out, and then all three collapsed down onto the bed. His hole had never felt so worn and abused, yet at the same time it had never felt so _good._

A few minutes passes in near silence save for the sound of them breathing heavily, before Sam noticed Dean’s dick was still half-hard. He reached out to gently touch it, causing Dean to draw a sharp intake of breath. “Need that taking care of?” he offered quietly, but all Dean managed in reply was a tired moan.

Taking that as a “yes,” Dean found himself being rolled onto his back, staring up at the ceiling while stars danced across his vision, and then something warm and wet was lapping across his dick. His cock immediately jumped to attention, rapidly hardening despite his balls twinging in protest, and then he let out another gasp when he felt a second mouth add to the sensation. Both Sam and Cas took care to share him with their mouths as they had with their hands, tasting every part of him, ensuring they sucked and licked at every sensitive spot under Dean was whimpering and trembling and his dick finally gave another twitch and spilled the remaining contents of his balls over his own chest.

Dizzy with pleasure, Dean managed nothing more than a soft mewl of, “ _Oh fuck…_ ”

He heard a soft chuckle from Cas as the angel crawled up the bed to lie down beside his head. “How was that for a reward, Dean?” the angel asked, and it was a fight for Dean to answer coherently.

“Fucking _awesome,_ ” he moaned softly. “Thank you, Cas, Sam.”

“You deserved it,” Cas said proudly, casting his gaze appreciatively over Dean’s naked body and the mess he was covered in. Honestly, the angel thought that when Dean looked as debauched as this he was at his most beautiful.

Beside him, Sam was lying exhausted and spent, face buried in the mattress. Cas smiled at the thought they’d both been satisfied so completely.

“Do I need a shower now?” Dean asked quietly after a few minutes, well aware of the sticky mess he was in and knowing his two doms would have to wash him.

“Yes,” Cas answered bluntly, but cast a hesitant glance at Sam’s exhausted form on Dean’s opposite side. “Sam, you want to go get him cleaned up? We can both do it.”

“Nnn,” came the muffled reply, the hunter evidently as worn out as his brother. “In the morning.”

Cas had to agree that might be for the best. It was especially nice now, he thought, how they both seemed to be getting to share Dean equally rather than taking turns. It was nice when they both got their fair share of Dean’s hole, Dean’s dick, getting to shower him, to feed him…all without the arguments. Things really were better with three.

“Alright,” the angel said softly, noticing Dean’s eyes had slipped shut already. He probably wouldn’t have made it as far as the bathroom if they’d tried. Cas leaned in to press an affectionate kiss against his forehead, draping an arm over Dean’s waist to rest on Sam’s hip on the other side. “Get some sleep, Dean. You’ve earned it. We’ll both be here in the morning.”

Proving he wasn’t quite asleep already, a small smile curved on Dean’s lips as he felt both his angel and his brother shuffle closer to him, before finally allowing himself to drift off into a contented, blissful sleep.


	25. Epilogue

**Notes for the Chapter:**

> Can a story be fairly said to have an epilogue when it never really had much of a plot to begin with? Well, I'm writing one. It's been a hell of a ride, but I think it's time I brought some closure to this story and wrapped things up. I feel like I've been playing kink bingo and won several times over, but there's still many squares left to fill. The story may be over, but the series most definitely isn't and I'll add to it as and when, but I also need time to focus on other things.
> 
> I'd just like to extend my heartfelt gratitude to everyone who's supported this story, and thank you so much for all your feedback, comments, praise, criticism, advice, corrections, kudos, and any other way in which you've lent support. I never imagined this story would quite kick off the way it did. It began as a distraction for myself during exams and a challenge to see how many kinks I could fit into one fic, and I think the answer is quite a lot. I've had a blast writing this and I'm enormously grateful for all the support it's received. If I managed to bring enjoyment or entertainment to people besides myself in the process of writing this, then it's been a worthwhile endeavour. If you've gotten far enough to read this, thank you all for sticking with me, and though you're unlikely to see it, thank you everyone who may have dropped off along the way too.

It’s been three weeks – three glorious, mind-spinning, taxing, blissful, perfect weeks – before their arrangement comes to a temporary end. Dean simultaneously feels like he’s been pampered and fawned over like a princess and pushed to right to his limits, but there’s nothing about it that he’d change.

A great sense of disappointment settles over him when Sam comes to tell him they’ve found a case to work, and they need to put things on hold. No distractions. No sex on the job. That was an agreement they’d reached a long time ago. It’s strange when he has to go offer his cock to Sam and Cas for the cage to come off and just…be normal. It’s not a scene. It’s not sex. The cage is just coming off. And then when Sam pats his arm and tells him, “Go get dressed,” it’s even stranger to be putting on his own jeans, his own t-shirt, and he’s wearing _clothes_ again.

It feels strange, unreal almost, when he’s left to do things on his own and has to bring his own bag out to the Impala, most definitely _not_ packed with any sex toys.

Cas seems to notice his unsettled expression as he dumps his stuff in the trunk. “You can jerk off now, you know,” he points out when Dean clambers into the driver’s seat. “That’s the point. No distractions. You don’t have to ask permission. Everything’s on hold. If you’re not satisfied, you can do whatever you need to.”

“I know,” Dean answers, “but it’s just…strange, y’know? I’m not sure that I want to.”

“Seriously, Dean,” Sam inputs, “If you need to jack off after having the cage on, you can. You don’t even need to ask. Whatever helps keep you focused.”

“Yeah, I know. But…” Dean turns in his seat to glance back at Cas as well as at Sam, making sure he’s addressing them both. “What we’ve got going on…it’s been great. Hell, _better_ than great. I don’t want to spoil it just because we’re on a break. Having you two get along like this…I couldn’t have asked for more, and I’m grateful. Really, I am. That’s why I don’t want to do it. I’m going to wait. Until you two can touch me again, I’m not going to touch myself. I’ve decided.”

Sam shrugs, but Dean could swear there’s a look of pride in the small smile his brother’s giving him. “Whatever works for you Dean; don’t feel that you _have_ to do it. But we appreciate that.” The look he exchanges with Cas warms Dean’s heart.

“Alright,” Dean says, turning back to face the road. “Down to business then.” As he sets off, everything begins to feel more natural again the further he drives, getting back into the swing of being on a hunt. He thinks he can do this: save himself for Sam and Cas for a few days. He’ll have enough to keep him occupied in the meantime, and it only makes him more excited to know what’s waiting for him when they get back.


End file.
